Karina Nguyen leads research at OpenAI, where she’s been pivotal in developing groundbreaking products like Canvas, Tasks, and the o1 language model. Before OpenAI, Karina was at Anthropic, where she led post-training and evaluation work for Claude 3 models, created a document upload feature with 100,000 context windows, and contributed to numerous other innovations. With experience as an engineer at the New York Times and as a designer at Dropbox and Square, Karina has a rare firsthand perspect...
Feb 09, 2025•1 hr 15 min•Transcript available on Metacast Tobi Lütke is the founder and CEO of Shopify, a $130 billion business that powers over 10% of all U.S. e-commerce. Starting as a snowboard shop in 2004, Shopify has become the leading commerce platform by consistently approaching problems differently. Tobi remains deeply technical, frequently coding alongside his team, and is known for his unique approach to leadership, product development, and company building. In our conversation, we discuss: • Why complexity kills entrepreneurship • How to de...
Feb 02, 2025•2 hr 42 min•Transcript available on Metacast Nan Yu is the head of product at Linear, one of the most beloved and fastest-growing B2B SaaS products out there today, and the gold standard for high-performing tech teams. In our conversation, we discuss: • Why speed and quality aren’t actually at odds • Linear’s unique approach to product development • Nan’s systematic approach to creativity • Linear’s philosophy on deadlines • The “double triangle” framework for product management • Nan’s approach to landing his dream product roles • Much mo...
Jan 30, 2025•1 hr 21 min•Transcript available on Metacast Chandra Janakiraman is the chief product officer, executive vice president, and a board member at VRChat. Previously, he was a product leader at Meta, where he led Facebook’s social experience interfaces and Reality Labs’ growth; served as CPO at Headspace, where he helped relaunch the platform, driving a 4x subscriber boost; and was a GM at Zynga, delivering massive hit games that reached hundreds of millions. In our conversation, Chandra shares: • His playbook for developing a product strategy...
Jan 26, 2025•2 hr 47 min•Transcript available on Metacast Elena Verna is one of Silicon Valley’s most sought-after growth advisors and operators. She previously led growth at companies like Amplitude, Miro, Dropbox, and SurveyMonkey and is currently doing full-time advising for high-growth tech companies. In our conversation, Elena and I discuss: • 10 growth tactics that never work • Her 3 favorite growth frameworks • How to increase your career optionality — Brought to you by: • Sinch —Build messaging, email, and calling into your product • Vanta —Aut...
Jan 19, 2025•2 hr 35 min•Transcript available on Metacast Graham Weaver teaches a top-rated course at Stanford’s Graduate School of Business (GSB), where he often unexpectedly ends up helping students figure out what to do with their lives. He is also the founder and CEO of Alpine Investors, a people-driven private equity firm. In our conversation, we discuss: • Why everything worthwhile requires suffering • Why most people operate on autopilot, and how to break free • The “genie methodology” for discovering your true path • The Nine Lives exercise for...
Jan 16, 2025•1 hr 12 min•Transcript available on Metacast Rohini Pandhi is a product leader at Mercury, and previously spent over seven years at Square/Block leading product work on Square payments, invoicing, and the Bitkey hardware Bitcoin wallet. She’s also the co-founder of the startup bootcamp Transparent Collective and is an active angel investor. In our conversation, we discuss: • Key indicators that it’s time to hire PMs • How to build your early PM team • Why founders should initially take on the product manager role themselves • How to attrac...
Jan 12, 2025•1 hr 19 min•Transcript available on Metacast Drew Houston is the co-founder and CEO of Dropbox. Under his leadership, Dropbox has grown from a simple idea to a service used by over 700 million registered users globally, with a valuation exceeding $9 billion. Drew has led Dropbox through multiple phases, from explosive viral growth, to battling all the tech giants at once, to reinventing the company for the future of work. In our conversation, he opens up about: • The three eras of Dropbox’s growth and evolution • The challenges he’s faced ...
Jan 09, 2025•2 hr 38 min•Transcript available on Metacast Alisa Cohn is an executive coach who has worked with C-suite executives at startups like Venmo, Etsy, Wirecutter, and DraftKings, and Fortune 500 companies like Microsoft, Google, Pfizer, Dell, and IBM. Inc. Magazine named Alisa one of the top 100 leadership speakers, and she was named one of the Top 50 coaches in the world by Thinkers50 and the #1 startup coach for the past four years by Global Gurus. She is also the author of From Start-Up to Grown-Up , which won the 2022 Independent Press Awa...
Jan 05, 2025•1 hr 24 min•Transcript available on Metacast Eilon Reshef is the co-founder and chief product officer at Gong, one of the most ubiquitous B2B products in the world. In our conversation, we discuss: • Gong’s unique approach to working with design partners • Their unique pod model • Why Eilon makes big decisions quickly • Lessons learned from being early in AI • The power of extreme focus • His “spiral method” for learning complex topics quickly • How to maintain quality while optimizing for speed — Brought to you by: • WorkOS —Modern identi...
Jan 02, 2025•57 min•Transcript available on Metacast Shaun Clowes is the chief product officer at Confluent and former CPO at Salesforce’s MuleSoft and at Metromile. He was also the first head of growth at Atlassian, where he led product for Jira Agile and built the first-ever B2B growth team. In our conversation, we discuss: • Why most PMs are bad, and how to fix this • Why great AI products are all about the data • Why he changed his mind about being data-driven • How to build your B2B growth team • How to choose your next career stop • Much mor...
Dec 29, 2024•1 hr 22 min•Transcript available on Metacast Marc Benioff is the co-founder and CEO of Salesforce, the second-largest software company in the world. He started programming at age 15, selling his first program for $75, and went on to build Salesforce into a company worth more than $300 billion that also owns Slack, Tableau, Quip, and MuleSoft. Marc is known as a marketing legend, and is now leading Salesforce into the era of AI agents. In our conversation, we discuss: • The importance of maintaining a beginner’s mind • His approach to produ...
Dec 22, 2024•57 min•Transcript available on Metacast Farhan Thawar is the head of engineering at Shopify, where he oversees more than 1,000 engineers and a platform that powers over 10% of all U.S. e-commerce. Before Shopify, he was VP of engineering at Pivotal Labs and Xtreme Labs, and co-founder of Helpful.com. In our conversation, Farhan shares: • Why choosing the harder path leads to better outcomes • How to create intensity within your org (without burnout) • Why every company should be embracing pair programming • How he hires without interv...
Dec 19, 2024•2 hr 40 min•Transcript available on Metacast Jackson Shuttleworth is a Group PM at Duolingo, where he leads the retention team and the powerful streak feature. The streak feature, which gamifies consecutive days of learning, has been Duolingo’s most important and innovative growth lever and a key driver of their growth to a $14 billion business with almost 600 million users. In our conversation, we dive deep into the history and lessons of this feature: • The evolution of the streak feature • Biggest insights from over 600 streak-related e...
Dec 15, 2024•1 hr 29 min•Transcript available on Metacast Seth Godin is a legend. He’s a marketer, teacher, entrepreneur, and author of more than 20 books, including Purple Cow , Permission Marketing , and Linchpin . He also writes one of the most popular and longest-running blogs in the world (approaching publishing 10,000 in a row !) and continues to shape how we think about marketing, brand, product, and creating lasting change in the world. In our conversation, we discuss: • How to build remarkable products that spread • The four critical strategic...
Dec 08, 2024•45 min•Transcript available on Metacast Jonathan Lowenhar is the co-founder of Enjoy The Work, an executive coaching firm that helps founders become great CEOs. Over the past decade, Enjoy The Work has supported over 165 founders on their journey to becoming better leaders. In our conversation, we discuss: • The difference between being a founder and being a CEO • Common failure modes for startup CEOs and how to avoid them • The four key elements of an effective go-to-market strategy • A framework for evaluating potential acquisitions...
Dec 05, 2024•2 hr 35 min•Transcript available on Metacast Michael Margolis has been a UX research partner at Google Ventures (GV) for nearly 15 years. He has developed a unique approach to helping startups identify their “bullseye customer”—the specific subset of their target market who initially is most likely to adopt their product. Michael has conducted over 300 hands-on research sprints with GV portfolio companies across various industries and helped develop the “design sprint” process made famous by the book Sprint . In our conversation, we discus...
Dec 01, 2024•2 hr 30 min•Transcript available on Metacast Jen Abel is the co-founder of JJELLYFISH, where she and her team have worked with over 300 early-stage founders to learn how to sell, do early customer discovery, and set up a repeatable sales motion on the way to their first $1M ARR. In our conversation, Jen shares: • Why founder-led sales is so crucial early on • The sales process, step by step • How to craft effective outreach messages • Where to find leads • What three channels work best for outreach • What to say on your first call • How to...
Nov 24, 2024•1 hr 16 min•Transcript available on Metacast Amjad Masad is the co-founder and CEO of Replit, a browser-based coding environment that allows anyone to write and deploy code. Replit has 34 million users globally and is one of the fastest-growing developer communities in the world. Prior to Replit, Amjad worked at Facebook, where he led the JavaScript infrastructure team and contributed to popular open-source developer tools. Additionally, he played a key role as a founding engineer at the online coding school Codecademy. In our conversation...
Nov 21, 2024•1 hr 4 min•Transcript available on Metacast Raaz Herzberg is the chief marketing officer and VP of product strategy at Wiz. Wiz hit $100 million ARR within 18 months (the fastest growth in startup history) and, five years in, is generating over $500 million ARR. It also serves over 45% of the Fortune 100. Raaz was one of the first five employees at Wiz, joining as the first product manager, and helped the team pivot to what may be the most intense PMF in history. Before Wiz, Raaz led security products at Microsoft, including Azure Sentine...
Nov 17, 2024•1 hr 5 min•Transcript available on Metacast Aman Khan is Director of Product at Arize AI, an observability company for AI engineers at companies like Uber, Instacart, and Discord. Previously he was an AI Product Manager at Spotify on the ML Platform team, enabling hundreds of engineers to build and ship products across the company. He has also led and worked on products at Cruise, Zipline, and Apple. In our conversation, we discuss: • What is an “AI product manager”? • How to break into AI PM • What separates top 5% AI PMs • How to thrive...
Nov 14, 2024•1 hr 18 min•Transcript available on Metacast Melissa Perri is the founder of Product Institute, author of Escaping the Build Trap , and host of the Product Thinking Podcast. She has worked with startups, Fortune 50 companies, and everything in between to help them build better products and level up their product teams. In our conversation, we discuss: • The history of the product owner role • The differences between product owners and product managers • How to transition from product owner to product manager • The evolution of and problems...
Nov 10, 2024•1 hr 24 min•Transcript available on Metacast Archie Abrams is the VP of Product and Head of Growth at Shopify, where he leads a 600+ person growth org across product, design, engineering, data, ops, and growth marketing. Shopify powers over 10% of e-commerce in the United States, with $235 billion in GMV in 2023 (roughly the size of Finland’s economy). He previously led Consumer product and growth at Lyft and was at Udemy for 8 years as SVP of Product having joined the company when it was 10 people. In our conversation, we discuss: • Why S...
Nov 07, 2024•1 hr 18 min•Transcript available on Metacast Alistair Croll is the co-author of the best-selling book Lean Analytics and a longtime product manager, entrepreneur, and startup advisor. He was also instrumental in my starting a company, funding it, and helping us exit to Airbnb as part of his Year One Labs incubator. He’s chaired notable events such as O’Reilly’s Strata and UBM’s Cloud Connect and founded FWD50. In our conversation, we focus on lessons from an upcoming book by Alistair and his co-author, Emily Ross, Just Evil Enough , which ...
Nov 03, 2024•1 hr 15 min•Transcript available on Metacast Shreyas Doshi is a former product leader at Stripe, Twitter, Google, and Yahoo. He’s now a full-time advisor and coach to founders and executives. Shreyas is known for his incredibly insightful writing on products, which has garnered him a passionate following in the PM and startup community. Last week, we sat down together at the very first Lenny and Friends Summit in San Francisco for a special live episode. We covered: • Why product leaders often feel overwhelmed with work, and how to combat ...
Oct 31, 2024•46 min•Transcript available on Metacast Naomi Gleit is head of product at Meta, joined as employee #29, and is the longest-serving executive at Meta other than Mark Zuckerberg. She’s been at the center of some of the company’s most foundational products, including Facebook’s early growth team. In our conversation, we discuss: • How she originally landed at Facebook • The evolution of Facebook’s growth team and key metrics • Lessons from working with Mark Zuckerberg • Insights from Facebook’s activation metric and retention strategies ...
Oct 27, 2024•2 hr 38 min•Transcript available on Metacast Jessica Hische is a lettering artist and New York Times bestselling author based in Oakland, California. She specializes in typographical work for logos, film, books, and other commercial applications. Her clients include Wes Anderson, The United States Postal Service, Target, Hallmark, and Penguin Books, and her work has been featured in design and illustration annuals both in the U.S. and internationally. She’s been named a Print Magazine New Visual Artist (20 under 30), one of Forbes 30 under...
Oct 20, 2024•1 hr 22 min•Transcript available on Metacast Anneka Gupta is the Chief Product Officer at Rubrik, a leading B2B cybersecurity company. She previously spent 11 years at LiveRamp, where she was the President and Head of Product and Platforms leading product development and go-to-market operations and strategy. Anneka also sits on the board of directors for Tinuiti and teaches product management at Stanford University. In our conversation, we discuss: • Navigating “founder mode” dynamics in organizations • Navigating difficult personalities a...
Oct 17, 2024•1 hr 9 min•Transcript available on Metacast Tristan de Montebello is the co-creator of Ultraspeaking, the most effective method I’ve come across for rapidly improving communication and presentation skills. In 2017, Tristan became the fastest person ever to reach the finals of the World Championship of Public Speaking, achieving this feat in just seven months with no prior experience. In our conversation, we discuss: • Why public speaking is a meta skill that can transform your life • Practical games and exercises to improve your speaking ...
Oct 13, 2024•2 hr 57 min•Transcript available on Metacast Raiza Martin is a senior product manager for AI at Google Labs, where she leads the team behind NotebookLM, an AI-powered research tool that includes a delightful podcast-on-demand feature called “Audio Overviews.” NotebookLM started as a 20% project and has grown into a product that’s spreading across social media and has a Discord server with over 60,000 users. Raiza previously worked on AI Test Kitchen and has a background in startups, payments, and ads. In our conversation, we discuss: • The...
Oct 10, 2024•49 min•Transcript available on Metacast 
