Best Lenny Rachitsky Podcasts (2026)

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The high-growth handbook: Molly Graham’s frameworks for leading through chaos, change, and scale 1:31:56

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18m ago1:31:56

1:31:56

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 for leaders navigating rapid scale, growth, and change. She’s best known for her “Give away your Legos” framework and her collection of practical mental models f…

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We replaced our sales team with 20 AI agents—here’s what happened | Jason Lemkin (SaaStr) 1:42:11

18m ago1:42:11

1:42:11

Jason Lemkin is the founder of SaaStr, the world’s largest community for software founders, and a veteran SaaS investor who has deployed over $200 million into B2B startups. After his last salesperson quit, Jason made a radical decision: replace his entire go-to-market team with AI agents. What started as an experiment has transformed into a new op…

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10 contrarian leadership truths every leader needs to hear | Matt MacInnis (Rippling) 1:36:17

4d ago1:36:17

1:36:17

Matt MacInnis is the chief product officer and former longtime COO at Rippling, a unified workforce management platform valued at over $16 billion. We discuss: 1. Why “extraordinary results demand extraordinary efforts” 2. Why you should deliberately understaff projects, and how to know when you’ve gone too far 3. Matt’s transition from COO to CPO …

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The coming AI security crisis (and what to do about it) | Sander Schulhoff 1:32:41

4d ago1:32:41

1:32:41

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 s…

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The new AI growth playbook for 2026: How Lovable hit $200M ARR in one year | Elena Verna (Head of Growth) 1:31:55

10d ago1:31:55

1:31:55

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…

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Why humans are AI’s biggest bottleneck (and what’s coming in 2026) | Alexander Embiricos (OpenAI Codex Product Lead) 1:25:13

11d ago1:25:13

1:25:13

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 soft…

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The 100-person AI lab that became Anthropic and Google's secret weapon | Edwin Chen (Surge AI) 1:10:31

18d ago1:10:31

1:10:31

Edwin Chen is the founder and CEO of Surge AI, the company that teaches AI what’s good vs. what’s bad, powering frontier labs with elite data, environments, and evaluations. Surge surpassed $1 billion in revenue with under 100 employees last year, completely bootstrapped—the fastest company in history to reach this milestone. Before founding Surge,…

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Why LinkedIn is turning PMs into AI-powered "full stack builders” | Tomer Cohen (LinkedIn CPO) 1:07:32

21d ago1:07:32

1:07:32

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 AI makes possible. Under his leadership, LinkedIn has scrapped its traditional Associate Product Manager program and replaced it with an Associate Product Builder…

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What world-class GTM looks like in 2026 | Jeanne DeWitt Grosser (Vercel, Stripe, Google) 1:26:02

25d ago1:26:02

1:26:02

Jeanne DeWitt Grosser built world-class GTM teams at Stripe, Google, and, most recently, Vercel, where she serves as COO and oversees marketing, sales, customer success, revenue operations, and field engineering. She transformed Stripe’s early sales organization from the ground up and advises founders on GTM strategy. We discuss: 1. Why GTM is beco…

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A guide to difficult conversations, building high-trust teams, and designing a life you love | Rachel Lockett 1:45:19

1M ago1:45:19

1:45:19

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 c…

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Slack founder: Mental models for building products people love ft. Stewart Butterfield 1:30:35

1M ago1:30:35

1:30:35

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, he’s been focused on family, philanthropy, and creative projects. In this rare podcast appearance, Stewart shares the product frameworks and leadership principl…

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The Godmother of AI on jobs, robots & why world models are next | Dr. Fei-Fei Li 1:19:34

2M ago1:19:34

1:19:34

Dr. Fei-Fei Li is known as the “godmother of AI.” She’s been at the center of AI’s biggest breakthroughs for over two decades. She spearheaded ImageNet, the dataset that sparked the deep-learning revolution we’re living right now, served as Google Cloud’s Chief AI Scientist, directed Stanford’s Artificial Intelligence Lab, and co-founded Stanford’s…

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“Dumbest idea I’ve heard” to $100M ARR: Inside the rise of Gamma | Grant Lee (CEO) 1:53:54

1M ago1:53:54

1:53:54

Grant Lee is the co-founder of Gamma, the AI-powered presentation tool that’s one of the hottest and most interesting AI startups in the world right now. They’re valued at over $2 billion, and they hit $100 million ARR in just over two years, with a lean team of just around 30 people. Unlike many fast-growing AI startups, Gamma has been profitable …

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"Sell the alpha, not the feature": The enterprise sales playbook for $1M to $10M ARR | Jen Abel 1:21:35

2M ago1:21:35

1:21:35

Jen Abel is GM of Enterprise at State Affairs and co-founded Jellyfish, a consultancy that helps founders learn zero-to-one enterprise sales. She’s one of the smartest people I’ve ever met on learning enterprise sales, and in this follow-up to our first chat two years ago (covering the zero to $1 million ARR founder-led sales phase), we focus on th…

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The woman behind Canva shares how she built a $42B company from nothing | Melanie Perkins 1:06:10

2M ago1:06:10

1:06:10

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, eight consecutive years of profitability. But the journey was far from smooth. Melanie was rejected by over 100 investors during her first fundraising ro…

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How Block is becoming the most AI-native enterprise in the world | Dhanji R. Prasanna 1:26:41

2M ago1:26:41

1:26:41

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 one of the most AI-native large companies in the world. Before becoming CTO, Dhanji wrote an “AI manifesto” to CEO Jack Dorsey that sparked a company-wide transfo…

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Al Engineering 101 with Chip Huyen (Nvidia, Stanford, Netflix) 1:22:35

2M ago1:22:35

1:22:35

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 read books on AI, including AI Engineering, which has been the most-read book on the O’Reilly platform since its launch. Unlike many AI commentators, Chip has bui…

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How to measure AI developer productivity in 2025 | Nicole Forsgren 1:07:48

2M ago1:07:48

1:07:48

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 book, Frictionless, a practical guide for helping teams move faster in the AI era. She’s currently Senior Director of Developer Intelligence at Google. We discuss:…

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Figma’s CEO: Why AI makes design, craft, and quality the new moat for startups | Dylan Field 1:26:49

3M ago1:26:49

1:26:49

Dylan Field is co-founder and CEO of Figma, a beloved tool used by every modern product team. Founded in 2012, Figma has expanded from a single design tool to a comprehensive platform including FigJam, Slides, Dev Mode, and, most recently, Figma Make. After a $20 billion acquisition by Adobe fell through due to regulatory pushback, Dylan led the co…

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Inside Google's AI turnaround: The rise of AI Mode, strategy behind AI Overviews, and their vision for AI-powered search | Robby Stein (VP of Product, Google Search) 1:21:37

3M ago1:21:37

1:21:37

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 led consumer products at Instagram, where he and his teams built Stories, Reels, Close Friends, and other key features now used by billions. — What you’ll learn: …

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First interview with Scale AI’s CEO: $14B Meta deal, what’s working in enterprise AI, and what frontier labs are building next | Jason Droege 1:24:01

3M ago1:24:01

1:24:01

Jason Droege is the CEO of Scale AI, a company that provides foundational training data to every major AI lab. He previously co-founded Scour with Travis Kalanick and built Uber Eats from idea to $20 billion in revenue. In this conversation, Jason shares lessons from getting sued for $250 billion, discovering restaurant economics by weighing sandwi…

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How to find hidden growth opportunities in your product | Albert Cheng (Duolingo, Grammarly, Chess.com) 1:25:25

3M ago1:25:25

1:25:25

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!), Albert developed a unique approach to finding and scaling growth opportunities through rapid experimentation and deep user psychology. His teams run 1,000 ex…

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A 4-step framework for building delightful products | Nesrine Changuel (Spotify, Google, Skype) 1:24:22

3M ago1:24:22

1:24:22

Nesrine Changuel helped build Spotify, Google Chrome, and Google Meet. Her work has helped her discover the importance of emotional connection in building successful products. At Google, she served as a dedicated “delight PM,” a role specifically focused on making products more delightful. She recently published Product Delight, a book that provide…

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Why AI evals are the hottest new skill for product builders | Hamel Husain & Shreya Shankar (creators of the #1 eval course) 1:46:33

3M ago1:46:33

1:46:33

Hamel Husain and Shreya Shankar teach the world’s most popular course on AI evals and have trained over 2,000 PMs and engineers (including many teams at OpenAI and Anthropic). In this conversation, they demystify the process of developing effective evals, walk through real examples, and share practical techniques that’ll help you improve your AI pr…

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From managing people to managing AI: The leadership skills everyone needs now | Julie Zhuo (Facebook VP, Sundial CEO, The Making of a Manager author) 1:36:24

3M ago1:36:24

1:36:24

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. Also, my first-ever podcast guest over 3 years ago! In our conversation, we discuss: 1. The three core manager skills that translate directly to managing AI ag…

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Why experts writing AI evals is creating the fastest-growing companies in history | Brendan Foody (CEO of Mercor) 1:06:39

3M ago1:06:39

1:06:39

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 founder ever. Mercor works with 6 of the Magnificent 7 and all top 5 AI labs to help them hire experts to create evaluations and training data that improve…

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The ultimate guide to AEO: How to get ChatGPT to recommend your product | Ethan Smith (Graphite) 1:11:55

4M ago1:11:55

1:11:55

Ethan Smith is the CEO of Graphite—the leading SEO growth agency—and my go-to expert on SEO. After 18 years of mastering traditional SEO, Ethan has been at the forefront of what is called AEO: answer engine optimization, or, more simply, getting your product to show up in ChatGPT/Claude/Gemini/Perplexity answers. He’s discovered that ChatGPT traffi…

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$46B of hard truths from Ben Horowitz: Why founders fail and why you need to run toward fear (a16z co-founder) 1:37:59

4M ago1:37:59

1:37:59

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 Loudcloud public with just $2 million in revenue (dubbed “the IPO from hell”), sold it for $1.6 billion, and has backed companies from Facebook to Stripe to Air…

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How AI is reshaping the product role | Oji and Ezinne Udezue 1:18:22

4M ago1:18:22

1:18:22

Ezinne and Oji Udezue have over 50 years of combined product leadership experience at Microsoft, Twitter, Atlassian, WP Engine, Typeform, and Calendly. They’ve witnessed every major shift in product management, and, despite their seniority, they’re taking beginner AI courses and learning from engineers half their age, and Oji is coding more now tha…

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How we restructured Airtable’s entire org for AI | Howie Liu (co-founder and CEO) 1:40:41

4M ago1:40:41

1:40:41

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’…

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How 80,000 companies build with AI: products as organisms, the death of org charts, and why agents will outnumber employees by 2026 | Asha Sharma (CVP of AI Platform at Microsoft) 57:11

4M ago57:11

57:11

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 more than 15,000 startups and enterprises. Before Microsoft, Asha was COO at Instacart, and VP of Product & Engineering at Meta, notably leading product for Messen…

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Inside the expert network training every frontier AI model | Garrett Lord (Handshake CEO) 1:09:50

4M ago1:09:50

1:09:50

Garrett Lord is co-founder and CEO of Handshake, which started as a career network for college students and new grads but recently discovered something extraordinary: they were sitting on the world’s largest network of academic experts—exactly what frontier AI labs desperately needed. With 500,000 PhDs and 3 million advanced degree holders creating…

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How Intercom rose from the ashes by betting everything on AI | Eoghan McCabe (founder and CEO) 1:23:20

4M ago1:23:20

1:23:20

Eoghan McCabe is the founder and CEO of Intercom, a customer service platform that has successfully pivoted to become an AI-first company with its agent product, Fin. After stepping away from the CEO role in 2020 due to health issues, Eoghan returned to find the company’s growth had stalled. Just one month after his return, ChatGPT launched, and wi…

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Why ChatGPT will be the next big growth channel (and how to capitalize on it) | Brian Balfour (Reforge) 1:29:11

5M ago1:29:11

1:29:11

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 to Google—and he’s spotted a pattern that’s about to repeat with ChatGPT. In this conversation, you’ll learn: 1. The 4-step cycle every platform follows (and …

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The one question that saves product careers | Matt LeMay 1:32:09

5M ago1:32:09

1:32:09

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 and authored two essential PM books, including Impact-First Product Teams. After watching countless product teams get laid off despite “doing everything right,” he …

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Inside ChatGPT: The fastest-growing product in history | Nick Turley (Head of ChatGPT at OpenAI) 1:35:38

5M ago1:35:38

1:35:38

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 shipped ChatGPT in just 10 days, helped it grow from zero to billions in revenue, and leads product for what may be the most consequential product of our time. …

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Brian Chesky's secret mentor who died 9 times, started the Burning Man board, and built the world's first midlife wisdom school | Chip Conley (founder of MEA) 1:19:36

5M ago1:19:36

1:19:36

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 the young founders on leadership and culture while learni…

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He saved OpenAI, invented the “Like” button, and built Google Maps: Bret Taylor on the future of careers, coding, agents, and more 1:28:57

5M ago1:28:57

1:28:57

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, and founding three companies. Today he’s the founder and CEO of Sierra, an AI agent company transforming customer service. He’s one of the few people I’ve met wh…

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Pricing your AI product: Lessons from 400+ companies and 50 unicorns | Madhavan Ramanujam 1:11:43

5M ago1:11:43

1:11:43

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 their pricing strategies. He’s the author of the definitive book on pricing, Monetizing Innovation. Now he’s back with a sequel, Scaling Innovation, which reveals…

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Anthropic co-founder on quitting OpenAI, AGI predictions, $100M talent wars, 20% unemployment, and the nightmare scenarios keeping him up at night | Ben Mann 1:14:59

6M ago1:14:59

1:14:59

Benjamin Mann is a co-founder of Anthropic, an AI startup dedicated to building aligned, safety-first AI systems. Prior to Anthropic, Ben was one of the architects of GPT-3 at OpenAI. He left OpenAI driven by the mission to ensure that AI benefits humanity. In this episode, Ben opens up about the accelerating progress in AI and the urgent need to s…

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The AI-native startup: 5 products, 7-figure revenue, 100% AI-written code | Dan Shipper (co-founder/CEO of Every) 1:34:57

6M ago1:34:57

1:34:57

Dan Shipper is the co-founder and CEO of Every. With just 15 people, Every publishes a daily AI newsletter, ships multiple AI products, and operates a million-dollar-a-year consulting arm—all while their engineers write virtually zero code. It’s the most radical example of AI-first operations, and Dan is a prolific writer who has become a leading v…

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Rapidly test and validate any startup idea with the 2-day Foundation Sprint (from the creators of the Design Sprint) | Jake Knapp & John Zeratsky (Character Capital) 1:41:33

6M ago1:41:33

1:41:33

Jake Knapp and John Zeratsky are the co-creators of the Design Sprint (the famous five-day product innovation process) and authors of the bestselling book Sprint. After decades of working with over 300 startups in the earliest stages, they discovered that most startups fail not because they can’t build, but because they build the wrong thing. The v…

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Solo founder, $80M exit, 6 months: The Base44 bootstrapped startup success story | Maor Shlomo 1:31:50

6M ago1:31:50

1:31:50

Maor Shlomo is the founder of Base44, an AI-powered app builder that he bootstrapped to an over $80 million acquisition by Wix in just six months. As a solo founder (with severe ADHD), he hit $1 million ARR just three weeks after launch and grew the product to more than 400,000 users, all while navigating two wars in Israel and never raising a doll…

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I’ve run 75+ businesses. Here’s why you’re probably chasing the wrong idea. | Andrew Wilkinson (co‑founder of Tiny) 1:28:28

6M ago1:28:28

1:28:28

Andrew Wilkinson is the co‑founder of Tiny, a holding company that quietly owns more than three dozen profitable internet and consumer brands, including Dribbble and the AeroPress coffee maker. Starting as a teenage barista and web designer, he’s created a portfolio approaching $300 million in yearly sales (and he was personally worth over $1 billi…

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Naming expert shares the process behind creating billion-dollar brand names like Azure, Vercel, Windsurf, Sonos, Blackberry, and Impossible Burger | David Placek (Lexicon Branding) 1:22:43

6M ago1:22:43

1:22:43

David Placek is the founder of Lexicon Branding, a company that focuses exclusively on the development of brand names for competitive advantage. Lexicon is behind iconic names such as Sonos, Microsoft’s Azure, Windsurf, Vercel, Impossible Foods, BlackBerry, Intel’s Pentium, Apple’s PowerBook, and Swiffer. Over 40 years, David’s team has named nearl…

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From ChatGPT to Instagram to Uber: The quiet architect behind the world’s most popular products | Peter Deng 1:55:28

6M ago1:55:28

1:55:28

Peter Deng has led product teams at OpenAI, Instagram, Uber, Facebook, Airtable, and Oculus and helped build products used by billions—including Facebook’s News Feed, the standalone Messenger app, Instagram filters, Uber Reserve, ChatGPT, and more. Currently he’s investing in early-stage founders at Felicis. In this episode, Peter dives into his mo…

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AI prompt engineering in 2025: What works and what doesn’t | Sander Schulhoff (Learn Prompting, HackAPrompt) 1:37:46

6M ago1:37:46

1:37:46

Sander Schulhoff is the OG prompt engineer. He created the very first prompt engineering guide on the internet (two months before ChatGPT’s release) and recently wrote the most comprehensive study of prompt engineering ever conducted (co-authored with OpenAI, Microsoft, Google, Princeton, and Stanford), analyzing over 1,500 academic papers and cove…

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How to build a team that can “take a punch”: A playbook for building resilient, high-performing teams | Hilary Gridley (Head of Core Product, Whoop) 1:54:39

7M ago1:54:39

1:54:39

Hilary Gridley is the Head of Core Product at WHOOP and a passionate thought leader in leveraging AI to elevate product teams and management practices. With extensive experience tackling challenging problems in regulated industries and high-stakes environments, Hilary emphasizes the importance of building resilience and adaptability within teams. P…

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35 years of product design wisdom from Apple, Disney, Pinterest, and beyond | Bob Baxley 1:41:59

7M ago1:41:59

1:41:59

Bob Baxley is a design leader who has shaped products used by billions at Apple, Pinterest, Yahoo, and ThoughtSpot. During his eight years at Apple, he led design for the online store and the App Store, and witnessed the iPhone’s transformative launch while working under Steve Jobs. A student of history turned software craftsman, Bob discovered his…

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How Mercado Libre built Latin America's most valuable company: 18k engineers, 30k deploys a day, and their own fleet of planes | Sebastian Barrios 1:19:25

7M ago1:19:25

1:19:25

Sebastian Barrios was the longtime head of product and engineering at Mercado Libre, the largest company in Latin America—valued at over $100 billion and home to more than 100,000 employees. There, he led a team of more than 18,000 engineers across 18 countries and oversaw an astonishing 30,000 code deployments a day. Before Mercado Libre, he found…