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Lenny's Podcast: Product | Growth | Career podcast cover art

Lenny's Podcast: Product | Growth | Career

ByLenny Rachitsky
268 episodes

Podcast Summary

Dive into "Lenny's Podcast: Product | Growth | Career," where innovation meets insight through conversations with industry titans. This podcast uniquely blends actionable advice with personal stories from top minds in product management and growth. Guests like Sachin Kansal, Uber's Chief Product Officer, share invaluable lessons on overseeing multifaceted platforms, while Krithika Shankarraman, former marketing lead at OpenAI and Stripe, offers a behind-the-scenes look at driving growth in cutting-edge tech environments. Each episode unpacks the strategies, challenges, and triumphs that shape successful careers in tech, making it a must-listen for aspiring entrepreneurs and seasoned professionals alike. Whether you’re looking to launch a product or enhance your career trajectory, Lenny's candid discussions provide the tools and inspiration needed to excel. Tune in for a wealth of knowledge that transforms complex concepts into relatable, actionable insights—because in the world of product and growth, every episode is a masterclass.

#1

Why Uber’s CPO delivers food on weekends | Sachin Kansal

Sachin Kansal is chief product officer at Uber, where he oversees the Rider, Driver, Delivery, Grocery, and New Verticals product lines used for 33 million daily trips worldwide. He’s been in product for over 25 years (at Google, Palm, Flywheel, and now Uber). He is known for his “extreme dogfooding” ethos—personally completing almost a thousand Uber driving and delivery trips to sharpen his product insight and user empathy—and his “ship, ship, ship” mantra, which drives rapid iteration across Uber’s global teams.What you will learn:Dogfooding at scale“Ship, ship, ship” as a cultural mantraObsession with inputs over outputsUber’s hybrid marketplace vision for autonomyHow Uber changed its culture to focus on profitabilityWhat to do when data says “no” but your gut says “yes”Career advice: maximize cyclesAI as a research assistant, not an oracleUber rider etiquette tips—Transcript: to you by:Paragon—Ship every SaaS integration your customers wantStripe—Financial infrastructure to grow your revenueCoda—The all-in-one collaborative workspace—Where to find Sachin Kansal:• LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Sachin’s background(05:00) Dogfooding in practice(11:24) Empathy and understanding drivers(20:18) Balancing metrics and user experience(22:04) Operationalizing dogfooding(24:26) Challenges and solutions in dogfooding(29:49) The motto: “ship, ship, ship”(36:37) Product announcements and live demos(40:49) Career advice for product managers(43:51) The evolution of product management with AI(46:55) Collaboration between engineers and product managers(49:36) Uber’s vision for self-driving cars(55:59) Uber’s path to profitability(01:01:58) Balancing data and gut decisions(01:07:21) AI tools in product management(01:10:14) Failure corner(01:13:48) Lightning round and final thoughts—Referenced:• Uber: Oracle: Snowflake: Fivetran: Uber for Business: McDonald’s: Domino’s: PalmPilot: Praveen Neppalli Naga on LinkedIn: May Mobility...

2025-06-01•1hr 21mins
#2

Growth tactics from OpenAI and Stripe’s first marketer | Krithika Shankarraman

Krithika Shankarraman was the first marketing hire at OpenAI and Stripe and led marketing at Retool. At OpenAI, she established marketing foundations for ChatGPT for consumers and enterprises, as well as their developer API platform. While at Stripe, she spent over eight years building and scaling their marketing function from scratch. An engineer turned marketer, Krithika brings a uniquely analytical approach to marketing. She currently serves as Entrepreneur in Residence at Thrive Capital, where she helps portfolio companies on all things marketing.What you will learn:Why do most marketing playbooks often fail, and what’s a better way?Which marketing lever should I pull first?Why is trying to be better than competitors usually a losing strategy?How do I craft positioning that actually converts?What makes messaging stick with developers, enterprises, and consumers?What pricing experiments actually move revenue?What is working at OpenAI really like?Why does consistency and quality matter more than speed?—Transcript: to you by:• Eppo—Run reliable, impactful experiments• Airtable ProductCentral—Launch to new heights with a unified system for product development• LinkedIn Ads—Reach professionals and drive results for your business—Where to find Krithika Shankarraman:• X: LinkedIn: Website: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Krithika(04:22) Early marketing lessons from OpenAI(11:17) Diagnosing marketing needs(15:06) The DATE framework and why being cheaper is a race to the bottom(17:11) Marketing strategies at Retool(22:29) Insights from marketing at Stripe(32:33) The importance of consistent marketing communication(39:55) Criteria for hiring a marketing expert(41:43) “Capital M” vs. “lowercase m” marketing(43:05) ChatGPT vs. Claude: market dominance(45:31) The future of AI and its societal impact(47:09) Work-life balance(48:41) Transitioning to Thrive(52:35) Career advice for marketers(55:00) The importance of tas...

2025-05-25•1hr 14mins
#3

Unconventional product lessons from Binance, N26, Google, more | Mayur Kamat (CPO at N26, ex-Binance Head of Product)

Mayur Kamat is the chief product officer at N26—a $9 billion neobank serving over 7 million customers in 25 countries—where he leads product, design, data, and research. Prior to N26, Mayur was Head of Product at Binance, growing the crypto exchange to a peak $400 billion valuation. Earlier in his career, he built and scaled products at Google (Gmail Mobile, Hangouts), Microsoft, and travel unicorn Agoda.Learn:How to find and focus on the highest-leverage problemsWhy you shouldn’t optimize for compensation early in your careerWhy you should optimize for strengths, not weaknessesWhy you need to decide if you truly want the C-suite pathWhy working at a fintech company creates exceptional PMsStrategy = hypothesis × experimentation velocitySmall, fast wins compound faster than big, slow bets—Transcript: to you by:⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs⁠Paragon⁠—Ship every SaaS integration your customers want⁠Vanta⁠—Automate compliance. Simplify security.—Where to find Mayur Kamat:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction and Mayur’s background(04:49) Working at Binance: An inside look(18:18) Career advice for product managers(27:00) PM career paths(33:58) Understanding fintech customers(36:00) Understanding your strengths(44:46) Creating a culture of experimentation(51:14) Hiring and developing top talent(54:50) Building a diverse product portfolio(57:08) Working in high talent density areas(59:43) Personal and professional balance(01:06:32) High-leverage opportunities and decision making(01:14:28) AI tools in the workplace(01:19:14) Failure corner(01:25:11) Lightning round and final thoughts—Referenced:• Binance: Google: Microsoft: Agoda: N26: Which companies accelerate PM careers most: Which companies produce the best product managers: Bezos Says Work-Life Balance is a “Debilitating” Phrase: Maslow’s Hierarchy of Needs: PayPal Mafia: Changpeng Zhao on LinkedIn: Ray Dalio on ...

2025-05-22•1hr 37mins
#4

Microsoft CPO: If you aren’t prototyping with AI you’re doing it wrong | Aparna Chennapragada

Aparna Chennapragada is the chief product officer of experiences and devices at Microsoft, where she oversees AI product strategy for their productivity tools and work on agents. Previously, she was the CPO at Robinhood, spent 12 years at Google, and is also on the board of eBay and Capital One.What you’ll learn:How “prompt sets are the new PRDs” and why prototyping with AI is now essential for effective product developmentThe three key characteristics of AI agents: autonomy (delegation of tasks), complexity (handling multi-step challenges), and natural interaction (conversing beyond simple chat)Why NLX (natural language experience) is the new UX, requiring deliberate design principles for conversational interfacesWhy the PM role isn’t dying in the AI era—it’s evolving to emphasize tastemaking and editingHow living “one year in the future” can be operationalized with programs like Microsoft’s FrontierHow even traditional enterprises can balance cutting-edge AI adoption with appropriate governance through dual-track approachesInsights on leadership differences between Microsoft’s Satya Nadella (known for multi-level thinking and early trendspotting) and Google’s Sundar Pichai (mastery of complex ecosystems)The vision for human and AI collaboration in the workplace, where people and agents achieve outcomes greater than either could aloneA practical framework for evaluating zero-to-one product opportunities—Transcript: to you by:• Eppo—Run reliable, impactful experiments• Pragmatic Institute—Industry‑recognized product, marketing, and AI training and certifications• Coda—The all-in-one collaborative workspace—Where to find Aparna Chennapragada:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Aparna Chennapragada(04:28) Aparna’s stand-up comedy journey(07:29) Transition to Microsoft and enterprise insights(10:00) The Frontier program and AI integration(13:28) Understanding AI agents(17:59) NLX is the new UX(22:28)...

2025-05-18•1hr 1mins
#5

How Revolut trains world-class product managers: The “local CEO” model, raw intellect over experience, and a cultural obsession with building wow products | Dmitry Zlokazov (Head of Product)

Dmitry Zlokazov is the head of product at Revolut, the $45 billion fintech giant operating in over 50 countries, serving more than 50 million customers, and producing some of the world’s top product leaders. Dmitry shares his hard-won lessons, contrarian org design principles, and day-to-day practices that power Revolut’s relentless shipping velocity, culture of ownership, and unparalleled “wow” product experience.What you’ll learn:Revolut’s unique organizational approach, where “product owners” manage cross-functional pods as “local CEOs,” with genuine end-to-end ownership and hiring/firing powerHow a radical, ultra-flat structure enables more than 150 product owners to maintain founder-level quality and velocity across dozens of parallel launchesHow Revolut maintains quality while shipping hundreds of features across over 50 countriesWhy Revolut favors “raw intellect and hunger” over experience, and how internal transfers (including ex-engineers and ops managers) become the company’s most successful product leadersHow Revolut’s founders review every single UI shipped, and why this founder detail obsession scales rather than limits innovationTheir framework for launching new products—from ideation, validation, and first user cohort to rapid “algorithmization” and scaling across countriesThe importance of treating products that are 99% done as closer to 0% done, vs. 100% done—Transcript: entire episode is brought to you by:Stripe—Helping companies of all sizes grow revenue—Where to find Dmitry Zlokazov:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Dmitry and Revolut(03:41) Revolut’s unique approach to product management(06:58) The role and responsibilities of product owners(09:28) Types of product owners at Revolut(15:50) Building “wow” products(25:00) Hiring practices(31:33) Managing teams and projects(41:07) Revolut’s diverse product offerings(44:40) Scaling new products successfully(52:10) Attracting top...

2025-05-15•1hr 10mins
#6

How Palantir built the ultimate founder factory | Nabeel S. Qureshi (founder, writer, ex-Palantir)

Nabeel Qureshi is an entrepreneur, writer, researcher, and visiting scholar of AI policy at the Mercatus Center (alongside Tyler Cowen). Previously, he spent nearly eight years at Palantir, working as a forward-deployed engineer. His work at Palantir ranged from accelerating the Covid-19 response to applying AI to drug discovery to optimizing aircraft manufacturing at Airbus. Nabeel was also a founding employee and VP of business development at GoCardless, a leading European fintech unicorn.What you’ll learn:Why almost a third of all Palantir’s PMs go on to start companiesHow the “forward-deployed engineer” model works and why it creates exceptional product leadersHow Palantir transformed from a “sparkling Accenture” into a $200 billion data/software platform company with more than 80% marginsThe unconventional hiring approach that screens for independent-minded, intellectually curious, and highly competitive peopleWhy the company intentionally avoids traditional titles and career ladders—and what they do insteadWhy they built an ontology-first data platform that LLMs loveHow Palantir’s controversial “bat signal” recruiting strategy filtered for specific talent typesThe moral case for working at a company like Palantir—Transcript: to you by:⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs⁠Attio⁠—The powerful, flexible CRM for fast-growing startups⁠OneSchema⁠—Import CSV data 10x faster—Where to find Nabeel S. Qureshi:• X: LinkedIn: Website: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Nabeel S. Qureshi(05:10) Palantir’s unique culture and hiring(13:29) What Palantir looks for in people(16:14) Why they don't have titles(19:11) Forward-deployed engineers at Palantir(25:23) Key principles of Palantir's success(30:00) Gotham and Foundry(36:58) The ontology concept(38:02) Life as a forward-deployed engineer(41:36) Balancing custom solutions and product vision(46:36) Advice on how to implement forward-d...

2025-05-11•1hr 37mins
#7

How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.In our conversation, we cover:A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilienceWhy teams most often fail (hint: it’s not lack of talent or strategy)How busyness often masks deeper issues of self-worthWhy a “growth mindset” can be problematicThe importance of legacy and what it means to live a meaningful lifeThe role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spotsJerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity—Transcript: ⁠ to you by:⁠⁠Eppo⁠⁠—Run reliable, impactful experiments⁠⁠Contentsquare⁠⁠—Create better digital experiences⁠⁠OneSchema⁠⁠—Import CSV data 10x faster—Where to find Jerry Colonna:• X: ⁠ LinkedIn: ⁠ Website: ⁠ to find Lenny:• Newsletter: ⁠ X: ⁠ LinkedIn: ⁠ this episode, we cover:(00:00) Introduction to Jerry Colonna(04:12) Jerry’s key question(06:55) The equation for great leadership(09:37) The big lie of success and happiness(12:12) The consciousness hack(15:56) Getting over the fear of consequences(20:23) The problem with bypassing our childhood baggage(23:22) Radical self-inquiry: asking the tough questions(27:05) Shared experiences: the power of communit...

2025-05-08•1hr 22mins
#8

Inside Devin: The world’s first autonomous AI engineer that's set to write 50% of its company’s code by end of year | Scott Wu (CEO and co-founder of Cognition)

Scott Wu is the co-founder and CEO of Cognition, the company behind Devin—the world’s first autonomous AI software engineer. Unlike other AI coding tools, Devin works like an autonomous engineer that you can interact with through Slack, Linear, and GitHub, just like with a remote engineer. With Scott’s background in competitive programming and a previous AI-powered startup, Lunchclub, teaching AI to code has become his ultimate passion.What you’ll learn:How a team of “Devins” are already producing 25% of Cognition’s pull requests, and they are on track to hit 50% by year’s endHow each engineer on Cognition’s 15-person engineering team works with about five Devins eachHow Devin has evolved from a “high school CS student” to a “junior engineer” over the past yearWhy engineering will shift from “bricklayers” to “architects”Why AI tools will lead to more engineering jobs rather than fewerHow Devin creates its own wiki to understand and document complex codebasesThe eight pivots Cognition went through before landing on their current approachThe cultural shifts required to successfully adopt AI engineers—Transcript: to you by:⁠• Enterpret⁠—Transform customer feedback into product growth⁠• Paragon⁠—Ship every SaaS integration your customers want• ⁠Attio⁠—The powerful, flexible CRM for fast-growing startups—Where to find Scott Wu:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Scott Wu and Devin(09:13) Scaling and future prospects(10:23) Devin's origin story(17:26) The idea of Devin as a person(22:19) How a team of “Devins” are already producing 25% of Cognition’s pull requests(25:17) Important skills in the AI era(30:21) How Cognition’s engineering team works with Devin's(34:37) Live demo(42:20) Devin’s codebase integration(44:50) Automation with Linear(46:53) What Devin does best(52:56) The future of AI in software engineering(57:13) Moats and stickiness in AI(01:01:57) The tech that enables Devin(01:04:14) AI will...

2025-05-04•1hr 32mins

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#9

The rise of Cursor: The $300M ARR AI tool that engineers can’t stop using | Michael Truell (co-founder and CEO)

Michael Truell is the co-founder and CEO of Anysphere, the company behind Cursor—the fastest-growing AI code editor in the world, reaching $300 million in annual recurring revenue just two years after its launch. In this conversation, Michael shares his vision for the future, lessons learned, and advice for preparing for the fast-approaching AI future.What you’ll learn:Cursor's early pivot from automating CAD to automating codeMichael’s vision for “what comes after code” and how programming will evolveWhy Cursor built their own custom AI models despite not starting thereKey lessons from Cursor’s rapid growthWhy “taste” and logic design will become more valuable engineering skills than technical coding abilityWhy the market for AI coding tools is much larger than people realize—and why there will likely be one dominant winnerMichael’s advice for engineers and product teams preparing for the AI future—Brought to you by:⁠Eppo⁠—Run reliable, impactful experiments⁠Vanta⁠—Automate compliance. Simplify security⁠OneSchema⁠—Import CSV data 10x faster—Where to find Michael Truell:• X: LinkedIn: Website: this episode, we cover:(00:00) Introduction to Michael Truell and Cursor(04:20) What comes after code(08:32) The importance of taste(12:39) Cursor’s origin story(18:31) Why they chose to build an IDE(22:39) Will everyone become engineering managers?(24:31) How they decided it was time to ship(26:45) Reflecting on Cursor's success(32:03) Counterintuitive lessons on building AI products(34:02) Inside Cursor's stack(38:42) Defensibility and market dynamics in AI(46:13) Tips for using Cursor(51:25) Hiring and building a strong team(59:10) Staying focused amid rapid AI advancements(01:02:31) Final thoughts and advice for aspiring AI innovators—Referenced:• Cursor: Microsoft Copilot: Scaling laws for neural language models: MIT: Telegram: Signal: WhatsApp: Devin: Visual Studio Code: Chromium: Exploring ChatGPT (GPT) Wrappers—What They Are and How They Work: OpenAI’s CPO on how AI...

2025-05-01•1hr 11mins
#10

Inside monday.com’s transformation: radical transparency, impact over output, and their path to $1B ARR | Daniel Lereya (Chief Product and Technology Officer)

Daniel Lereya, the Chief Product and Technology Officer at monday.com, shares how he and his team realized they were being outpaced by competitors and how that realization completely transformed how they operate and allowed them to build a global powerhouse, doing over $1 billion in ARR, with 245,000 customers worldwide.What you’ll learn:How they used seemingly impossible goals, like building 25 new features in one month, to unlock bigger thinking on their teamHow sharing real-time metrics with the entire company—even during interviews—created a culture of accountability and alignmentHow focusing on impact, rather than just shipping features, has transformed the company’s cultureThe story behind monday.com’s decision to launch five new products simultaneously and how it redefined their market positioningHow they use “traps” (timeboxed deadlines) to drive focus, avoid scope creep, and deliver fasterDaniel’s personal journey of navigating impostor syndrome and scaling challenges, and the mental models he uses to stay grounded and effective—Transcript: to you by:• Enterpret—Transform customer feedback into product growth• Airtable ProductCentral—Launch to new heights with a unified system for product development• Vanta—Automate compliance. Simplify security—Where to find Daniel Lereya:• LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Daniel and monday.com(04:20) The pivotal moment: competitors shipping faster(08:50) Setting ambitious goals(17:44) Focusing on impact rather than features(27:07) Transforming your product quarterly(32:07) Scaling monday.com: challenges and strategies(39:14) How monday.com maintains transparency as a public company(45:40) The importance of taking risks(51:02) Counterintuitive lessons in product development(54:33) The value of timeboxing and deadlines(57:28) Embracing user feedback(59:54) Adapting leadership styles(01:04:43) Personal reflections on leadership(01:10:41) Handling crises and ...

2025-04-27•1hr 32mins
#11

Introducing How I AI with Claire Vo

AI is rapidly changing how we live and work. It’s exciting, but also overwhelming. If you’re struggling to keep up, and wondering how to actually use these magical new tools to improve the quality and efficiency of your work, I’m thrilled to introduce How I AI with Claire Vo—the first ever new podcast under the Lenny’s Podcast network. Claire is an engineer, three-time CPO, and AI builder. In each episode, her guest shows you a specific, practical, and impactful way they’ve learned to use AI. Forget theoretical debates—this podcast is about real, valuable use cases. Expect 30-minute episodes, live demos, and tips/tricks/workflows you can implement immediately. Whether you’re building products, leading teams, or just looking to level up your AI skills, How I AI is for you.SUBSCRIBE TO THE SHOW→ YouTube: Spotify: ⁠ Apple:

2025-04-22•47mins
#12

Building a magical AI code editor used by over 1 million developers in four months: The untold story of Windsurf | Varun Mohan (co-founder & CEO)

Varun Mohan is the co-founder and CEO of Windsurf (formerly Codeium), an AI-powered development environment (IDE) that has been used by over 1 million developers in just four months and has quickly emerged as a leader in transforming how developers build software. Prior to finding success with Windsurf, the company pivoted twice—first from GPU virtualization infrastructure to an IDE plugin, and then to their own standalone IDE.In this conversation, you'll learn:Why Windsurf walked away from a profitable GPU infrastructure business and bet the company on helping engineers codeThe surprising UI discovery that tripled adoption rates overnightThe secret behind Windsurf's B2B enterprise plan, and why they invested early in an 80-person sales team despite conventional startup wisdomHow non-technical staff at Windsurf built their own custom tools instead of purchasing SaaS products, saving them over $500k in software costsWhy Varun believes 90% of code will be AI-generated, but engineering jobs will actually increaseHow training on millions of incomplete code samples gives Windsurf an edge, and creates a moat long-termWhy agency is the most undervalued and important skill in the AI era—Transcript: to you by:⁠Brex⁠—The banking solution for startups⁠Productboard⁠—Make products that matter⁠Coda⁠—The all-in-one collaborative workspace—Where to find Varun Mohan:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Varun’s background(03:38) The origin story of Windsurf(04:46) Pivots and challenges faced(06:01) Building and scaling Windsurf(16:31) The future of engineering and AI(22:23) Hiring philosophy and company culture(34:39) Sales strategy and market position(39:09) JetBrains vs. VS Code: extensibility and enterprise adoption(40:46) Live demo: building an Airbnb for dogs with Windsurf(42:32) Tips for using Windsurf effectively(46:01) AI’s role in code modification and review(48:40) Empowering non-developers to build custom software(53:29)...

2025-04-20•1hr 14mins
#13

Everyone’s an engineer now: Inside v0’s mission to create a hundred million builders | Guillermo Rauch (founder & CEO of Vercel, creators of v0 and Next.js)

Guillermo Rauch is the founder and CEO of Vercel, creators of v0 (one of the most popular AI app building tools), and the mind behind foundational JavaScript frameworks like Next.js and Socket.io. An open source pioneer and legendary engineer, Guillermo has built tools that power some of the internet’s most innovative products, including Midjourney, Grok, and Notion. His mission is to democratize product creation, expanding the pool of potential builders from 5 million developers to over 100 million people worldwide. In this episode, you’ll learn:How AI will radically speed up product development—and the three critical skills PMs and engineers should master now to stay aheadWhy the future of building apps is shifting toward prompts instead of code, and how that affects traditional product teamsSpecific ways to improve your design “taste,” plus practical tips to consistently create beautiful, user-loved productsHow Guillermo built a powerful app in under two hours for $20 (while flying and using plane Wi-Fi) that would normally take weeks and thousands of dollars in engineering timeThe exact strategies Vercel uses internally to leverage AI tools like v0 and Cursor, enabling their team of 600 to ship faster and better than ever beforeGuillermo’s actionable advice on increasing your product quality through rapid iteration, real-world user feedback, and creating intentional “exposure hours” for your team—Transcript: to you by:⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs⁠Vanta⁠ — Automate compliance. Simplify security⁠LinkedIn Ads⁠—Reach professionals and drive results for your business—Where to find Guillermo Rauch:• X: LinkedIn: Website: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Guillermo Rauch(04:43) v0's mission(07:03) The impact and growth of v0(15:54) The future of product development with AI(19:05) Empowering engineers and product builders(24:01) Skills for the future: coding, math, and ...

2025-04-13•1hr 27mins
#14

OpenAI’s CPO on how AI changes must-have skills, moats, coding, startup playbooks, more | Kevin Weil (CPO at OpenAI, ex-Instagram, Twitter)

Kevin Weil is the chief product officer at OpenAI, where he oversees the development of ChatGPT, enterprise products, and the OpenAI API. Prior to OpenAI, Kevin was head of product at Twitter, Instagram, and Planet, and was instrumental in the development of the Libra (later Novi) cryptocurrency project at Facebook.In this episode, you’ll learn:How OpenAI structures its product teams and maintains agility while developing cutting-edge AIThe power of model ensembles—using multiple specialized models together like a company of humans with different skillsWhy writing effective evals (AI evaluation tests) is becoming a critical skill for product managersThe surprisingly enduring value of chat as an interface for AI, despite predictions of its obsolescenceHow “vibe coding” is changing how companies operateWhat OpenAI looks for when hiring product managers (hint: high agency and comfort with ambiguity)“Model maximalism” and why today’s AI is the worst you’ll ever use againPractical prompting techniques that improve AI interactions, including example-based prompting—Find the transcript at: to you by:⁠Eppo⁠—Run reliable, impactful experiments⁠Persona⁠—A global leader in digital identity verification⁠OneSchema⁠—Import CSV data 10x faster—Where to find Kevin Weil:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Kevin’s background(05:16) OpenAI’s new image model(08:13) The role of chief product officer at OpenAI(11:42) His recruitment story and joining OpenAI(15:59) Working at OpenAI(18:44) The importance of evals in AI(24:40) Opportunities in the space(26:34) Shipping quickly and consistently(29:47) Product reviews and iterative deployment(32:53) Winning consumer awareness(36:03) Designing thoughtful experiences (40:56) Chat as an interface for AI(45:21) Collaboration between researchers and product teams(48:05) Hiring product managers at OpenAI(53:06) How OpenAI uses AI: vibe coding, AI prototyping, and more(01:04:34) Raising kids in ...

2025-04-10•1hr 31mins
#15

Become a better communicator: Specific frameworks to improve your clarity, influence, and impact | Wes Kao (coach, entrepreneur, advisor)

Wes Kao is an entrepreneur, coach, and advisor. She co-founded the live learning platform Maven, backed by First Round and a16z. Before Maven, Wes co-created the altMBA with best-selling author Seth Godin. Today, Wes teaches a popular course on executive communication and influence. Through her course and one-on-one coaching, she’s helped thousands of operators, founders, and product leaders master the art of influence through clear, compelling communication. Known for her surgical writing style and no-BS frameworks, Wes returns to the pod to deliver a tactical master class on becoming a sharper, more persuasive communicator—at work, in meetings, and across your career.What you’ll learn:The communication mistake leaders make—and Wes’s proven fix to instantly gain buy-inWes’s MOO (Most Obvious Objection) framework to consistently anticipate and overcome pushback in meetingsHow to master concise communication—including Wes’s tactical approach for brevity without losing meaningThe art of executive presence: actionable strategies for conveying confidence and clarity, even under pressureThe “sales, then logistics” framework—and why your ideas keep getting ignored without itThe power of “signposting”—and why executives skim your docs without itExactly how to give feedback that works—Wes’s “strategy, not self-expression” principle to drive behavior change without frictionPractical ways to instantly improve your writing, emails, and Slack messages—simple techniques Wes teaches executivesManaging up like a pro: Wes’s clear, practical advice on earning trust, building credibility, and aligning with senior leadersCareer accelerators: specific habits and tactics from Wes for growing your influence, advancing your career, and standing outReal-world communication examples—Wes breaks down real scenarios she’s solved, providing step-by-step solutions you can copy today—Transcript: to you by:• WorkOS—Modern identity platform for B2B SaaS, free up to 1 million MAUs• Vanta—Automate...

2025-04-06•1hr 33mins
#16

A better way to plan, build, and ship products | Ryan Singer (creator of “Shape Up,” early employee at 37signals)

Ryan Singer is one of the earliest employees and the former Head of Strategy at 37signals (the makers of Basecamp), where he spent nearly two decades refining a product development approach that helped the company build super-successful products with small teams. Based on these lessons, he wrote "Shape Up: Stop Running in Circles and Ship Work that Matters," and Ryan now works with companies of all sizes to help them escape the cycle of endless sprints, missed deadlines, and dragging projects.What you’ll learn:Why traditional Agile and Scrum methods often lead teams into endless cycles of work without meaningful shipping milestones.The “appetite-driven” approach to product development where teams set fixed timeboxes (usually six weeks maximum) and vary the scope instead of expanding timelines.The exact process for running effective “shaping” sessions that collaboratively define projects before committing resources.Why most teams struggle with too little detail in their planning, not too much.Why a 30-to-50-person team size is the critical breaking point when growing startups need to adopt more structured processes.Practical techniques for bridging the engineering-design divide by bringing technical and product perspectives together earlier in the process.The powerful “breadboarding” and “fat marker sketching” techniques that help teams align on solutions without getting lost in high-fidelity details.The clear warning signs that your current development process is failing before it’s too late to change course.Proven strategies to implement Shape Up methods, whether you’re working in a startup or enterprise environment.A step-by-step approach to transitioning from Scrum to Shape Up by piloting the methodology with a single team before broader implementation.Why the PM role shifts upstream in Shape Up, focusing more on problem definition than project management.How to adapt Shape Up principles to your company’s unique context, even if it’s nothing like Basecamp.—Bro...

2025-03-30•1hr 45mins
#17

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)

Gaurav Misra is the co-founder and CEO of Captions, an AI-powered video creation company and one of the most successful consumer AI products in the world today. Previously he was a product leader at Snap, where he created the design engineering function and spent years helping develop features used by hundreds of millions of users worldwide. With a background in both engineering and design, Gaurav brings a unique cross-functional perspective to product development.What you’ll learn:Why the “ship a marketable feature every week” approach helps his team stay focused and the product stay top of mind for users amid constant AI breakthroughsHow to balance rapid shipping with maintaining quality by cutting scope rather than compromising on timelinesThe “secret roadmap” strategy that helps Captions develop breakthrough features competitors never see comingWhy taking on strategic technical debt is essential for startups to outpace larger companiesHow Captions accidentally ignored their most successful product for 1.5 years (and why it still grew to 500K users with no updates or support)How Snap’s unique product development approach—with designers functioning as PMs—enabled their success as the last major social network to break throughWhy AI video will transform marketing before other industries—Brought to you by:• ⁠Brex⁠ — The banking solution for startups• ⁠Paragon⁠—Ship every SaaS integration your customers want• ⁠Coda⁠—The all-in-one collaborative workspace—Find the transcript at: to find Gaurav Misra:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Gaurav’s background(04:47) The exciting era of AI and startups(09:30) Staying top of mind(11:26) Tips for staying focused(13:14) Shipping marketable features weekly(19:03) Managing technical debt in startups(25:31) Snap’s unique product development approach(32:09) Brainstorming with AI(35:09) What Snap got right(41:06) Scaling with a small, agile team(49:33) The shift toward prototypi...

2025-03-27•1hr 25mins
#18

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)

Rahul Vohra is the founder and CEO of Superhuman. Prior to Superhuman, Rahul founded Rapportive, the first Gmail plug-in to scale to millions of users, which he sold to LinkedIn in 2012. He is also a prominent angel investor, and his fund has invested $50 million in over 120 companies, including Placer, Supabase, Mercury, Zip, ClassDojo, and Writer.What you’ll learn:The unexpected insight about virality Rahul gained from LinkedIn’s head of growth.Why Rahul restructured his entire executive team to spend 60% to 70% of his time on product, design, and marketing instead of the typical CEO responsibilities.The counterintuitive approach to finding product-market fit using a methodical system inspired by Sean Ellis, and how this algorithmically determines your roadmap.How manually onboarding every user (Superhuman had 20 full-time people doing this at peak) created superfans and allowed engineers to focus on product rather than onboarding flows.The “Single Decisive Reason” framework for making better decisions by avoiding collections of weak justifications.How Superhuman’s AI features have evolved to create a truly intelligent email experience that works while you sleep.—Brought to you by:• ⁠Eppo⁠—Run reliable, impactful experiments• ⁠Fundrise Flagship Fund⁠—Invest in $1.1 billion of real estate• ⁠OneSchema⁠—Import CSV data 10x faster—Find the transcript at: to find Rahul Vohra:• X: LinkedIn: Email: [email protected]—Where to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Rahul and Superhuman(05:00) The most pivotal moment in Rahul's career(07:01) The secret to virality(11:02) Superhuman’s product evolution and core values(13:32) Overcoming slowdowns at scale(18:06) Time management and meditation(27:35) The role of a president(30:56) Attention to detail(43:00) Finding your unique position(47:32) The power of manual onboarding(52:37) Mastering product-market fit(59:33) Game design in business software(01:05:35) Contrarian pricing...

2025-03-23•1hr 25mins
#19

A field guide for introverts: How to thrive at work without changing who you are | Susan Cain (author of "Quiet")

Susan Cain, author of the groundbreaking bestseller Quiet: The Power of Introverts in a World That Can't Stop Talking, shares a guide for how introverts can thrive in the workplace without sacrificing their authentic selves. Drawing from her extensive research and personal experience, Cain offers a powerful reframing: success doesn't require becoming more extroverted—it demands becoming more fully yourself.—What you'll learn:A simple definition of introversion and how it differs from shyness—plus a simple two-question test to determine where you fall on the spectrum.Five practical tactics introverts can use to be more successful in business while staying true to their natural temperament.How to handle challenging workplace scenarios like meetings dominated by loud voices and networking events that drain your energy.Specific strategies for managers and founders to create environments where introverted team members can contribute their best work.Practical techniques for saying "no" to energy-draining commitmentsStrategies for managers to better support and leverage introverted team membersPractical advice for raising introverted children to help them develop confidence while honoring their natural temperament.Why seeking to become "more extroverted" is the wrong goal—and what to focus on instead to achieve professional success.—Brought to you by:• ⁠Enterpret⁠ — Transform customer feedback into product growth• ⁠Vanta⁠ — Automate compliance. Simplify security• ⁠Fundrise Flagship Fund⁠ — Invest in $1.1 billion of real estate—Find the transcript at: to find Susan Cain:• Substack: ⁠ X: LinkedIn: Website: Instagram: Facebook: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Susan Cain(03:55) Understanding introversion(07:35) The spectrum of introversion and extroversion(14:01) Overcoming public speaking anxiety(23:16) Strategies for introverts in business(32:43) Networking and saying no(40:43) Effective meeting participation for int...

2025-03-16•1hr 17mins
#20

Inside Bolt: From near-death to ~$40m ARR in 5 months—one of the fastest-growing products in history | Eric Simons (founder & CEO of StackBlitz)

Eric Simons is the founder and CEO of StackBlitz, the company behind Bolt—the web-based AI coding agent and one of the fastest-growing products in history. After nearly shutting down, StackBlitz launched Bolt on Twitter and exploded from zero to $40 million ARR and 1 million monthly active users in about five months.—What you’ll learn:How Bolt reached nearly $40M ARR and 3 million registered users in just five months with a team of only 15 to 20 peopleHow Bolt leverages WebContainer technology—a browser-based operating system developed over seven years—to create a dramatically faster, more reliable AI coding experience than competitorsWhy Anthropic’s 3.5 Sonnet model was the critical breakthrough that made AI-generated code production-ready and unlocked the entire text-to-app marketWhy PMs may be better positioned than engineers in the AI eraHow AI will dramatically reshape company org chartsEric’s wild founder story (including squatting at AOL’s HQ) and how scrappiness fueled his innovation—Brought to you by:• ⁠Eppo⁠—Run reliable, impactful experiments• ⁠Fundrise Flagship Fund⁠—Invest in $1.1 billion of real estate• ⁠OneSchema⁠—Import CSV data 10x faster—Find the transcript at: to find Eric Simons:• X: LinkedIn: Email: [email protected]—Where to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Eric Simons and StackBlitz(04:46) Unprecedented growth and user adoption(10:40) Demo: Building a Spotify clone with Bolt(15:28) Expanding to native mobile apps with Expo(19:09) The journey and technology behind WebContainer(25:03) Lessons learned and future outlook(29:15) Post-launch analysis(34:15) Growing fast with a small team(41:00) Prioritization at Bolt(45:51) Tooling and PRD's(48:42) Integration and use cases of Bolt(52:24) Limitations of Bolt(54:24) The role of PMs and developers in the AI era(59:56) Skills for the future(01:14:18) Upcoming features of Bolt(01:20:17) How to get the most out of Bolt(01:23:00) Eric’s journey and ...

2025-03-13•1hr 28mins
#21

Building Lovable: $10M ARR in 60 days with 15 people | Anton Osika (CEO and co-founder)

Anton Osika is the co-founder and CEO of Lovable, which is building what they call “the last piece of software”—an AI-powered tool that turns descriptions into working products without requiring any coding knowledge. Since launching three months ago, Lovable hit $4 million ARR in the first four weeks and $10 million ARR in two months with a team of just 15 people, making it Europe’s fastest-growing startup ever.What you’ll learn:Why you need to be in the top 1% of AI tool usersWatch Lovable build a functional Airbnb clone in 30 seconds—complete with working features and modern designThe unconventional hiring approach that helped build a 15-person team capable of extraordinary executionHow traditional product development will look with AIWhat skills will matter most to product teams going forwardHow Anton’s team discovered a breakthrough in AI “unsticking itself”—Brought to you by:• ⁠Sinch⁠—Build messaging, email, and calling into your product• ⁠Persona⁠—A global leader in digital identity verification• ⁠Fundrise Flagship Fund⁠—Invest in $1.1 billion of real estate—Find the transcript at: to find Anton Osika:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Anton and Lovable(05:12) Lovable’s rapid growth(09:39) Live demo: Building an Airbnb clone(18:34) Tips for mastering Lovable(21:42) The origin story(26:50) Scaling laws and getting AI unstuck(33:20) Reliability and unique features(36:25) The vision and future of Lovable(38:14) Skills and job market evolution in the age of AI(40:30) Hiring philosophy and team dynamics(46:21) Building in Europe(48:02) Prioritization and product roadmap(51:38) Tools and work environment(53:17) Tactics for moving fast(54:37) Advice for building product teams(57:11) Empowering non-technical founders(58:31) Future developments and user support(01:01:23) Failure corner(01:05:20) Final thoughts and advice—Referenced:• Lovable: Lovable Launched: Cloudflare: Supabase: GPT engineer: Mic...

2025-03-09•1hr 9mins
#22

Notion’s lost years, its near collapse during Covid, staying small to move fast, the joy and suffering of building horizontal, more | Ivan Zhao (CEO and co-founder)

Ivan Zhao is the co-founder and CEO of Notion. Ivan shares the untold story of Notion, from nearly running out of database space during Covid to finding product-market fit after several “lost years,” and the hard-won lessons along the way. What you’ll learn:Why you sometimes need to “hide your vision” behind something people actually want—what Ivan calls “sugar-coating the broccoli”How Ivan and his co-founder persevered through multiple product resets and complete code rewritesWhy Notion prioritized systems over headcount, keeping the team small and focused even at scaleWhy Ivan believes in craft and values as the foundation for product development, balancing technical excellence with aesthetic sensibilityThe surprising story of how Notion nearly collapsed during Covid when their single database almost ran out of space with only weeks to spareCommunity-led growth tacticsIvan’s unique journey from a small town in ChinaMuch more—Brought to you by:• ⁠Eppo⁠—Run reliable, impactful experiments• ⁠Airtable ProductCentral⁠—Launch to new heights with a unified system for product development• ⁠Sinch⁠—Build messaging, email, and calling into your product—Find the transcript at: to find Ivan Zhao:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Ivan Zhao(04:41) Ivan’s early life and education(07:46) Discovering the vision for Notion(10:49) The lost years of Notion(13:56) Rebuilding and perseverance(17:14) Layoffs and company morale(18:53) Advice for startup founders(25:08) Product-market fit(29:56) Staying lean and efficient(34:27) Creating a unique office culture(37:20) Craft and values: the foundation of Notion’s philosophy(38:44) Navigating tradeoffs in product and business building(41:24) Leadership and personal growth(49:11) Challenges and crises: lessons from Notion’s journey(51:08) Building horizontal software: joys and pains(01:02:40) Philosophy of tools and human potential(01:06:17) Lightning round and final thou...

2025-03-06•1hr 12mins
#23

The creator of WordPress opens up about becoming an internet villain, why he’s taking a stand, and the future of open source | Matt Mullenweg (founder and CEO, Automattic)

Matt Mullenweg is the co-founder of WordPress, the open source platform powering a staggering 43% of the internet. He also serves as CEO of Automattic—the parent company of brands like WordPress.com, WooCommerce, and Tumblr—which is worth over $7 billion, with over 1,700 employees across 90 countries. In this episode, he discusses some of the most controversial topics surrounding WordPress, Automattic, and the broader open source community. What you’ll learn:Matt’s response to public criticismWhy products like Meta’s Llama are “fake open source”How his team is turning around Tumblr after acquiring it for just $3 million (after Yahoo bought it for $1.1 billion)Why he mortgaged his home to fund San Francisco’s iconic Bay Lights projectMatt’s philosophy: “Don’t just build a product; build a movement”Why open source matters: “If the Founding Fathers were around today, they’d be open source advocates”—Brought to you by:• ⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs• ⁠Vanta⁠—Automate compliance. Simplify security.• ⁠Loom⁠—The easiest screen recorder you’ll ever use—Find the transcript at: to find Matt Mullenweg:• X: LinkedIn: Instagram: Website: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Matt Mullenweg(05:10) Matt’s career journey(11:15) Bay Lights project and philanthropy(17:28) How Matt got involved with open source(23:25) Why products like Meta’s Llama are “fake open source”(27:14) The future of open source and how to get involved(35:25) Building a successful online community (39:12) The WP Engine controversy(50:24) Facing criticism and controversy(55:29) Addressing community concerns(01:08:29) Forking Advanced Custom Fields(01:11:15) The role of social media and public perception(01:16:43) Acquiring and reviving Tumblr(01:24:25) Automattic’s acquisition strategy(01:28:51) Final thoughts and future plans—Referenced:• WordPress: Automattic: CNET: Akismet: Jetpack: Toni Schneider on LinkedIn: Wo...

2025-03-02•1hr 34mins

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#24

An inside look at X’s Community Notes | Keith Coleman (VP of Product) and Jay Baxter (ML Lead)

Keith Coleman (VP of Product) and Jay Baxter (founding ML engineer), the minds behind Community Notes, reveal how a small, scrappy team inside Twitter/X built the most trusted crowdsourced information system on the internet—one that’s changing the way we understand truth online. What you’ll learn:How Community Notes actually works—a deep dive into the groundbreaking algorithm that rewards “bridging agreement” instead of majority ruleThe seemingly crazy yet brilliant way this idea survived multiple CEO changes—from Jack to Parag to ElonHow this project started with a dumpster fire GIF (literally)—the untold backstory of its early launchThe secret to running ultra-fast, high-impact product teams—no OKRs, no Jira; just one Google DocWhat Meta’s adoption of Community Notes means for the future of online (mis)information—why this open source system is becoming the industry standard—Brought to you by:• ⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs• ⁠Productboard⁠—Make products that matter• ⁠Wix Studio⁠—The web creation platform built for agencies—Find the transcript at: to find Keith Coleman:• X: LinkedIn: to find Jay Baxter:• X: LinkedIn: Website: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Community Notes(06:56) How the “bridging-based” algorithm works(13:33) The impact and scale of Community Notes(17:24) Understanding the note publishing threshold (21:32) Challenges and philosophies(26:26) The effect of notes on re-sharing content(29:41) Origin story(35:46) Embracing small teams for big impact(40:23) The thermal project approach(47:47) Algorithm development and internal competitions(50:34) An inside look at how the team operates (58:56) Working with Elon(01:05:30) Launching Birdwatch (01:10:48) The core principles behind Community Notes(01:26:15) Anonymity and pseudonymity in contributions(01:32:17) Sustaining the project through leadership changes(01:37:57) Future directions for Community Notes...

2025-02-27•1hr 47mins
#25

How to find work you love | Bob Moesta (Jobs-to-be-Done co-creator, author of "Job Moves”)

Bob Moesta, co-creator of the Jobs to Be Done framework, recently published a new book, Job Moves. Drawing from interviews with over 1,000 people about their career transitions, it offers a practical playbook for career development. In our conversation, we discuss:• ⁠⁠The four different “quests” that drive career changes• ⁠⁠Why job features (salary, title) matter less than experiences• ⁠⁠How to identify what gives you energy vs. drains you• ⁠⁠The power of taking a “jobcation”• ⁠⁠A template for crafting your career story• ⁠⁠Tips for hiring and retaining great talent• ⁠⁠The importance of prototyping potential careers• ⁠⁠Much more—Brought to you by:• ⁠Eppo⁠—Run reliable, impactful experiments• ⁠Vanta⁠—Automate compliance. Simplify security• ⁠OneSchema⁠—Import CSV data 10x faster—Find the transcript at: to find Bob Moesta:• X: LinkedIn: Website: Podcast: The Re-Wired Group: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Bob's background(05:10) Bob’s new book, Job Moves(09:31) Job features vs. job experiences (11:16) Four reasons people leave jobs(17:20) Energy drivers and energy drains(31:05) Prototyping your next job(34:32) Pushes and pulls(40:01) Understanding that no job is perfect(43:18) Taking a jobcation(51:22) Finding the right next step(55:18) Navigating job applications and interviews(58:28) How to craft your career story(01:04:04) Strengths and weaknesses: leveraging your superpowers(01:06:21) Hiring and writing job descriptions(01:11:20) Self-awareness and founding a startup(01:21:24) Conclusion and final thoughts—Referenced:• The ultimate guide to JTBD | Bob Moesta (co-creator of the framework): Ethan S. Bernstein on LinkedIn: National Geographic: Radical Candor: From theory to practice with author Kim Scott: Building a long and meaningful career | Nikhyl Singhal (Meta, Google): The Story Spine (also known as Pixar’s Story Structure): Tobi Lütke on LinkedIn: Job Moves resources: Why Employees Quit: book:• Job Moves: 9 Steps for Ma...

2025-02-23•1hr 24mins
#26

A founder’s guide to crisis management | Uri Levine (Waze co-founder, serial entrepreneur)

Uri Levine is a co-founder of Waze (which was acquired by Google for $1.3 billion in 2013), along with nine other companies (including another company he sold for over $1 billion). He’s also been on 20 boards and has been an advisor to over 50 startups. He recently released a new chapter of his best-selling book Fall in Love with the Problem, Not the Solution, which provides a guide to surviving crises at your company. In this episode, we cover:• The two types of startup crisis and how to handle them• Why speed of action is the most important thing• How to keep your team motivated when things look dire• A framework for deciding whether or not to pivot• What to do when product-market fit disappears• How to approach raising money during a crisis• More—Brought to you by:•⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs•⁠Rippling⁠—Automate HR, IT, and finance so you can scale faster•⁠OneSchema⁠—Import CSV data 10x faster—Find the transcript at: to find Uri Levine:• X: LinkedIn: Website: Book: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Welcome back, Uri!(05:10) The new chapter: navigating crises(08:15) Types of crises founders face(29:10) Navigating cash crises(38:31) The importance of never giving up(46:26) How to keep people engaged through a crises(47:59) Transparency in crisis management(56:58) Navigating product-market-fit challenges(59:27) Deciding when to pivot or shut down(01:13:34) Real-life startup survival stories(01:17:06) Avoiding and preparing for crises(01:21:21) Final thoughts and book promotion—Referenced:• Waze: Moovit: Order Chat: Fibo: Behind the founder: Drew Houston (Dropbox): TomTom: Khosla Ventures: WeSki: Larry Silverstein: Oversee: Lessons from 1,000+ YC startups: Resilience, tar pit ideas, pivoting, more | Dalton Caldwell (Y Combinator, Managing Director): Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and...

2025-02-16•1hr 23mins
#27

OpenAI researcher on why soft skills are the future of work | Karina Nguyen (Research at OpenAI, ex-Anthropic)

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 perspective on the cutting edge of AI and large language models. In our conversation, we discuss:• How OpenAI builds product• What people misunderstand about AI model training• Differences between how OpenAI and Anthropic operate• The role of synthetic data in model development• How to build trust between users and AI models• Why she moved from engineering to research• Much more—Brought to you by:•⁠Enterpret⁠—Transform customer feedback into product growth•⁠Vanta⁠—Automate compliance. Simplify security•Loom—The easiest screen recorder you’ll ever use—Find the transcript at: to find Karina Nguyen:• X: LinkedIn: Website: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Introduction to Karina Nguyen(04:42) Challenges in model training(08:21) Synthetic data and its importance(12:38) Creating Canvas(18:33) Day-to-day operations at OpenAI(20:28) Writing evaluations(23:22) Prototyping and product development(26:57) Building Canvas and Tasks(33:34) Understanding the job of a researcher (35:36) The future of AI and its impact on work and education(42:15) Soft skills in the age of AI(47:50) AI’s role in creativity and strategy development(53:34) Comparing Anthropic and OpenAI(57:11) Innovations and future visions(01:07:13) The potential of AI agents(01:11:36) Final thoughts and career advice—Referenced:• What’s in your stack: The state of tech tools in 2025: Anthropic: OpenAI: What is synthetic data—and how can it help you competitively?: GPQA: Canvas: Barret Zoph on ...

2025-02-09•1hr 14mins
#28

Tobi Lütke’s leadership playbook: Playing infinite games, operating from first principles, and maximizing human potential (founder and CEO of Shopify)

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 develop and leverage your unique talent stack • How specifically Tobi approaches thinking from first principles • The importance of focusing on unquantifiable qualities like joy and delight • Why Tobi works backward from a 100-year vision • Why metrics should support decisions, not make them • The power of following your curiosity • What Tobi believes it takes to be a great product leader • Much more — Brought to you by: • ⁠Sinch⁠—Build messaging, email, and calling into your product • ⁠Liveblocks⁠—Ready-made collaborative features to drop into your product • Loom—The easiest screen recorder you’ll ever use — Find the transcript at: — Where to find Tobi Lütke: • X: • LinkedIn: • Website: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Welcome and introduction (04:17) The Tobi tornado (07:10) Maximizing human potential (11:05) Education and personal growth (16:47) Operating without KPIs (25:00) First-principles thinking (40:04) Remote work (45:59) Why Tobi never stopped coding (54:46) Embracing disagreement (01:01:27) The 100-year vision (01:09:29) Balancing tactics and positioning (01:17:15) Encouraging entrepreneurship (01:19:34) The power of good UX (01:28:42) The talent stack and unique opportunities (01:34:30) The role of passion in product development (01:36:39) Final thoughts and farewell — Referenced: • How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng): • Breaking the rules of growth: Why Shopif...

2025-02-02•1hr 41mins
#29

Linear’s secret to building beloved B2B products | Nan Yu (Head of Product)

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 more — Brought to you by: • ⁠Sinch⁠—Build messaging, email, and calling into your product • ⁠Paragon⁠—Ship every SaaS integration your customers want • ⁠Wix Studio⁠—The web creation platform built for agencies — Find the transcript at: — Where to find Nan Yu: • X: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Introduction to Nan Yu and Linear (04:54) Survey insights: Linear vs. Jira (07:51) The speed vs. quality myth (09:24) Building and iterating quickly (15:31) Avoiding bloat in enterprise software (23:57) Understanding user needs deeply (30:09) How to approach customer calls (34:10) Creating strong emotional hooks (40:31) Managing the product backlog (44:46) Systemizing creativity (48:16) Demo: Saving drafts in Linear (51:38) Breaking constraints and building at extremes (54:15) Adopting new tools (58:22) The “double triangle” framework for product management (01:04:23) Effective job-hunting strategies for PMs (01:09:15) Thoughts on deadlines (01:14:15) Lightning round — Referenced: • Jira: • Linear: • Patrick Collison’s post on X: • Magnus Carlsen on X: • Hikaru Nakamura on X: • Geoffrey Moore on finding your beachhead, crossing the chasm, and dominating a market: • Customer Request feature on Linear: • Everlane: • Schlep Blindness: • Linear’s triage tool: • Patrick Collison’s post about mental models on X: • Brian Chesky’s new playbook: • Unpacking Amazon’s unique ways of working | Bill Carr (author of Working Bac...

2025-01-30•1hr 21mins
#30

An operator’s guide to product strategy | Chandra Janakiraman (CPO at VRChat, ex-Meta, Headspace, Zynga)

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 • The difference between “small s” and “big S” strategy • How to run strategy sprints • Who should be involved in strategy work • Common pitfalls in strategy development • The role of AI in future strategy development • More — Brought to you by: • ⁠Eppo⁠—Run reliable, impactful experiments • ⁠Airtable ProductCentral⁠—Launch to new heights with a unified system for product development • ⁠OneSchema⁠—Import CSV data 10x faster — Find the transcript at: — Where to find Chandra Janakiraman: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Chandra’s background (04:47) The importance of strategy (12:40) Defining product strategy (15:42) Developing a winning strategy: an overview (18:51) The preparation phase (30:46) The strategy sprint process (45:51) The design sprint (51:19) Document writing (57:39) Rolling out your strategy (01:01:28) Resourcing and roadmapping (01:04:42) Strategy lessons from Zynga (01:11:34) Strategy lessons from Meta (01:15:55) Big S strategy (01:26:58) AI in strategy formulation (01:38:12) Final thoughts and lightning round — Referenced: • Headspace: • Good Strategy, Bad Strategy | Richard Rumelt: • 5 essential questions to craft a winning strategy | Roger Martin (author, advisor, speaker): • VRChat: • Andrew Chen on LinkedIn: • Template: Working Backwards PR FAQ: • How LinkedIn became interesting: The inside story | Tomer Cohen (CPO at LinkedIn): • Making time for what matters | Jake Knapp and John Ze...

2025-01-26•1hr 47mins
#31

10 growth tactics that never work | Elena Verna (Amplitude, Miro, Dropbox, SurveyMonkey)

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—Automate compliance. Simplify security • ⁠OneSchema⁠—Import CSV data 10x faster — Find the transcript at: — Where to find Elena Verna: • Newsletter: • X: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Welcome back, Elena! (06:02) Common mistakes growth teams make (08:31) : Hiring for growth roles too soon (15:09) : Hiring a head of growth to fix your problems (19:20) : Doing a rebrand to drive growth (25:11) : Obsessing over your competition (34:00) : Believing that your problems are unique (42:32) : Prioritizing other growth channels above earned channels (50:55) : Failing to evolve your growth model (01:01:06) : Not hiring advisors (01:05:55) : Over-experimenting (01:10:44) : Color optimizations, third-party signups, one-email wonders, and removing friction (01:15:00) Elena’s favorite growth frameworks (01:18:50) Contrarian corner: full-time jobs (01:26:05) Lightning round and final thoughts — 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: • The ultimate guide to product-led sales | Elena Verna: • Six rules of hiring for growth: • Figma: • Miro: • Notion: • Carol Wong on LinkedIn: • Dropbox: • The Law of Shitty Clickthroughs: • Miroverse: • GitHub: • My 9 Favorite Growth Frameworks: • Growth Loops are the New Funnels: • Racecar Growth Framework: • The Adjacent User: • Unorthodox frameworks...

2025-01-19•1hr 35mins
#32

How to break out of autopilot and create the life you want | Graham Weaver (Stanford GSB professor, founder of Alpine Investors)

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 exploring different life possibilities • How to overcome limiting beliefs that hold you back • Why “not now” is often just another way of saying “never” • More — Brought to you by: • ⁠Merge⁠—A single API to add hundreds of integrations into your app • ⁠Persona⁠—A global leader in digital identity verification • ⁠Liveblocks⁠—Ready-made collaborative features to drop into your product — Find the transcript at: — Where to find Graham Weaver: • LinkedIn: • Instagram: • YouTube: • Website: • TikTok: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Graham’s background (05:30) Helping students find their true path (07:40) The genie methodology (12:36) Breaking free from autopilot mode (17:54) Identifying and overcoming limiting beliefs (20:33) Teaching entrepreneurship and personal fulfillment (22:53) The reality of long-term success (35:14) The role of accountability and executive coaching (40:22) Daily goal setting for success (43:11) The Nine Lives framework (48:01) The dangers of the “not now” mentality (55:27) Navigating life’s transitions (57:19) Failure corner (01:00:24) When to quit and when to persevere (01:02:18) Final thoughts and lightning round — Referenced: • Setting Goals: Demystified: • Tony Robbins’s website: • Alpine Investors: • Stanford GSB Last Lecture 2024—How to Live Your Life at Full Power: • I turned 50 today. Here is the most important thing I learned in my first half century: • Where the Crawdads Sing on Prime ...

2025-01-16•1hr 12mins
#33

How to build your product team from scratch, attract top product talent, go multi-product, and more | Rohini Pandhi (Mercury, Square)

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 attract top PM talent • What she’s learned about going multi-product • A case for investing in quality • More — Skip the Mercury Personal waitlist: — Brought to you by: • Cloudinary—The foundational technology for all images and video on the internet • OneSchema—Import CSV data 10x faster • Airtable ProductCentral—Launch to new heights with a unified system for product development — Find the transcript at: — Where to find Rohini Pandhi: • X: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Rohini’s background (05:00) The role of product managers at Mercury (09:51) Key indicators that it’s time to hire PMs (13:18) Building the product team at Mercury (19:53) Why you should avoid hiring PMs too early (22:26) The different flavors of product management (26:15) How to attract top talent (35:59) Advocating for quality in product development (44:10) Going multi-product (46:37) Organizational structure for multi-product success (50:57) Organizational culture for multi-product success (52:07) Customer obsession and product development (57:36) More lessons from going multi-product (01:05:57) Transparent Collective: supporting underrepresented founders (01:09:54) Lightning round — Referenced: • Immad Akhund on X: • Mercury: • Square: • Product management career ladders: • Pioneers, Settlers, Town Planners [Wardley]: • Jason Zhang on LinkedIn: • What is ‘Dogfooding’?: • Mercury Bill Pay: • Zip: • Jira: • The art and science of pricing |...

2025-01-12•1hr 19mins
#34

Behind the founder: Drew Houston (Dropbox)

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 over the past 18 years • What he learned about himself • How he’s been able to manage his psychology as a founder • The importance of maintaining your learning curve • Finding purpose beyond metrics and growth • The micro, macro, and meta aspects of building companies • Much more — Brought to you by: • ⁠Paragon⁠—Ship every SaaS integration your customers want • ⁠Explo⁠—Embed customer-facing analytics in your product • ⁠Vanta⁠—Automate compliance. Simplify security — Find the transcript at: — Where to find Drew Houston: • X: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Introduction to Drew and Dropbox (04:44) The three eras of Dropbox (07:53) The first era: Viral growth and early success (14:19) The second era: Challenges and competition (20:49) Strategic shifts and refocusing (29:36) Personal reflections and leadership lessons (40:19) Unlocking mindfulness and building support systems (43:14) The Enneagram test (50:35) The challenges of being a founder CEO (58:11) The third era: Rebooting the team and core business (01:22:41) Lessons and advice for aspiring founders (01:27:46) Balancing personal and professional growth (01:42:38) Final reflections and future outlook — Referenced: • Dropbox: • Y Combinator: • Paul Graham’s website: • Hacker News: • Arash Ferdowsi on LinkedIn: • Sequoia Capital: • Pejman Nozad on LinkedIn: • Mike Moritz on LinkedIn: • TechCrunch Disrupt: • Dropbox viral demo: • Digg: • Reddit: • Hadi ...

2025-01-09•1hr 47mins
#35

Scripts for difficult conversations: Giving hard feedback, navigating defensiveness, the three questions you should end every meeting with, more | Alisa Cohn (executive coach)

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 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 Award and the American Book Fest 2023 Best Book Award for Entrepreneurship, and is the creator and host of a podcast of the same name. In our conversation, we discuss: • The psychology behind why we avoid difficult conversations • Specific scripts for having five common difficult conversations • How to handle defensive reactions in the moment • The three questions you should end every meeting with • “The founder prenup” that every founding team should work through • Common leadership myths • Stories of failure from Alisa’s career — Brought to you by: • ⁠Eppo⁠—Run reliable, impactful experiments • ⁠Rippling⁠—Automate HR, IT, and finance so you can scale faster • ⁠Liveblocks⁠—Ready-made collaborative features to drop into your product — Find the transcript at: — Where to find Alisa Cohn: • X: • LinkedIn: • Website: • Podcast: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Alisa’s background (04:48) Having difficult conversations (12:48) Scripts for performance feedback (20:20) How to respond when someone is defensive or upset (25:07) Scripts for handling promotion disappointments (31:00) Scripts for handling terminations (35:44) The importance of positive feedback (38:49) Understanding your job as a leader (44:55) Recognizing your own blind spots (49:38) Three vital questions to ask in every meeting (55:57) The founder prenup (01:08:24) Failure corner (01:13:00) Final thoughts and lightning round — Referenced: • Alisa’s free PDF downloads...

2025-01-05•1hr 23mins
#36

Inside Gong: How teams work with design partners, their pod structure, autonomy, trust, and more | Eilon Reshef (co-founder and CPO)

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 identity platform for B2B SaaS, free up to 1 million MAUs • ⁠Think Fast Talk Smart⁠—Tools and techniques to help you communicate more effectively • ⁠Vanta⁠—Automate compliance. Simplify security — Find the transcript at: — Where to find Eilon Reshef: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Eilon’s background (04:20) The pod model (06:33) Working with design partners (09:13) Finding and coordinating design partners (13:12) Balancing customer feedback and vision (15:10) Gong's 95% feature adoption (17:05) The importance of autonomy and trust (23:30) How to implement this unique way of working (27:15) Speed and decision-making (31:47) Early AI adoption and lessons learned (35:50) Building effective AI teams (38:16) The spiral method for learning (41:36) Narrowing down the initial customer profile (44:24) Failure corner (46:35) Lightning round — Referenced: • Gong: • Cisco: • How Gong builds product: • What is Montessori education?: • Isaac Asimov: • Amit Bendov on LinkedIn: • Lessons from scaling Spotify: The science of product, taking risky bets, and how AI is already impacting the future of music | Gustav Söderström (Co-President, CPO, and CTO at Spotify): • Nvidia: • Figma: • The Spiral Method: • Webex: • L’Oréal: • American Express: • Slow Horses on AppleTV+: • Dishwasher basket: • What most people miss about marketing | Rory Sutherland (Vice Chairman of Ogilvy UK, author): • Occam’s razor: • Hanlon’s razor: • Sabi...

2025-01-02•56mins
#37

Why great AI products are all about the data | Shaun Clowes (CPO Confluent, ex-Salesforce, Atlassian)

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 more — Brought to you by: • ⁠Enterpret⁠—Transform customer feedback into product growth • ⁠BuildBetter⁠—AI for product teams • ⁠Wix Studio⁠—The web creation platform built for agencies — Find the transcript at: — Where to find Shaun Clowes: • X: • LinkedIn: • Website: • Reforge: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Shaun’s background (05:08) The state of product management (09:33) Becoming a 10x product manager (13:23) Specific ways to leverage AI in product management (17:15) Feedback rivers (19:20) AI's impact on data management (24:35) The future of enterprise businesses with AI (35:41) Data-driven decision-making (45:50) Building effective growth teams (50:18) The evolution of product-led growth (56:16) Career insights and decision-making (01:07:45) Failure corner (01:12:32) Final thoughts and lightning round — Referenced: • Steve Blank’s website: • Getting Out of the Building. 2 Minutes to See Why: • OpenAI: • Claude: • Sachin Rekhi on LinkedIn: • Video: Building Your Product Intuition with Feedback Rivers: • Confluent: • Workday: • Lenny and Friends Summit: • A conversation with OpenAI’s CPO Kevin Weil, Anthropic’s CPO Mike Krieger, and Sarah Guo: • Anthropic: • Salesforce: • Atlassian: • Jira: • Ashby: • Occam’s razor: • Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify): • Charli...

2024-12-29•1hr 21mins
#38

Behind the founder: Marc Benioff

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 product launches and marketing • ⁠⁠Managing through tough times and layoffs • ⁠⁠His relationship with Steve Jobs and lessons learned • ⁠⁠Why Salesforce is betting big on AI agents • ⁠⁠Many stories from his entrepreneurial roller coaster • ⁠⁠Much more — Brought to you by: • ⁠Cloudinary⁠—The foundational technology for all images and video on the internet • ⁠Enterpret⁠—Transform customer feedback into product growth • ⁠Coda⁠—The all-in-one collaborative workspace — Find the transcript at: — Where to find Marc Benioff: • X: • LinkedIn: — In this episode, we cover: (00:00) Introduction to Marc Benioff and Salesforce (03:54) Marc’s early career and domain names (05:59) The App Store story and lessons from Steve Jobs (15:18) Lessons from launching Salesforce (22:03) The importance of keeping a beginner’s mindset (29:53) Why Marc calls Salesforce the “25-year startup” (31:47) Agentforce (36:09) Why Marc says AI is the defining technology of our lifetime (40:12) AI’s impact on the workforce (42:31) Entrepreneurs need to be like conductors (46:02) Failure corner (50:32) The future of AI agents (56:34) Final thoughts and farewell — Referenced: • Bill.com: • App Store: • Salesforce: • Oracle: • Larry Ellison on X: • Siebel Systems: • Saba Software: • Tom Siebel on LinkedIn: • Avon: • Salesforce Chief Has Pulled Some Crazy Stunts: • Matthew McConaughey on Instagram: • Woody Harrelson on Instagram: • “Ask More of AI” with Matthew McConaughey: • Marc’s tweet about the ad with McConaughey...

2024-12-22•57mins
#39

How Shopify builds a high-intensity culture | Farhan Thawar (VP and Head of Eng)

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 interviewing • How he built the world’s largest internship program • His mission to create a “crafter’s paradise” for engineers • Much more — Brought to you by: • ⁠DX⁠—A platform for measuring and improving developer productivity • ⁠Persona⁠—A global leader in digital identity verification • ⁠Vanta⁠—Automate compliance. Simplify security — Find the transcript at: — Where to find Farhan Thawar: • X: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Farhan’s background (05:38) Choosing the hard path (09:37) Getting comfortable with looking dumb (13:20) Lessons from working with visionaries (19:19) Creating intensity in organizations (22:06) The power of pair programming (29:18) Shopify’s culture of intensity (37:18) Meeting Armageddon: revolutionizing company meetings (39:46) Reducing distractions (41:10) Deleting 1M+ lines of code (49:05) Three buckets of building (57:45) Remote work and trust battery (01:00:29) Finding stability in uncomfortable times (01:03:14) Hiring philosophy (01:11:41) Internship programs and co-op systems (01:15:32) Lessons from managing 120 direct reports (01:20:40) Failure corner (01:27:46) Lightning round and closing thoughts — Referenced: • The Steve Jobs quote about connecting dots: • Shopify: • GitHub: • Farhan’s “questions to ask” framework: • Palantir: • Joe Liemandt: • Chamath Palihapitya: • Xtreme Labs: • Parkinson’s law: • Pair programming: • Cody Fauser on LinkedIn: • How Shopify builds produ...

2024-12-19•1hr 40mins
#40

Behind the product: Duolingo streaks | Jackson Shuttleworth (Group PM, Retention Team)

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 experiments • ⁠⁠Biggest specific wins and misses along the way • ⁠⁠Key principles for building effective streak mechanics • ⁠⁠How to operate a high-velocity product team • ⁠⁠Tips for building engaging notification systems • ⁠⁠Much more — Brought to you by: • ⁠Pendo⁠—The only all-in-one product experience platform for any type of application • ⁠Vanta⁠—Automate compliance. Simplify security • ⁠Coda⁠—The all-in-one collaborative workspace — Find the transcript at: — Where to find Jackson Shuttleworth:• LinkedIn: — In this episode, we cover: (00:00) Jackson’s background and an overview of Duolingo’s streak feature (06:00) The impact of streaks on Duolingo’s success (09:58) The origin and evolution of streaks (14:50) Key experiments and insights (24:38) User psychology and engagement strategies (28:36) Duolingo’s product review structure (33:07) Designing for clarity and adaptability (46:59) Developing the Streak Freeze feature (50:47) Balancing monetization and retention (54:08) Notification strategies (58:15) The Perfect Streak feature (01:00:40) Enhancing the user experience (01:04:47) Team operations and experimentation (01:18:57) Who can benefit from streaks (01:21:00) Lightning round — Referenced: • Duolingo streaks: • How to make learning as addictive as social media: • Luis von Ahn on LinkedIn: • FarmVille: • Royal Match: • How Duolingo reignited user growth: • You’re on fire! Or, how we brought the streak milestone to life: • Duolingo Doubles Down on Design and Anim...

2024-12-15•1hr 28mins
#41

Seth Godin's best tactics for building remarkable products, strategies, brands and more

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 choices that determine your future • How to develop good taste and high standards • The role of tension in great strategy • How Seth used Claude to write his newest book • Much more — Brought to you by: • ⁠DX⁠—A platform for measuring and improving developer productivity • ⁠Vanta⁠—Automate compliance. Simplify security • ⁠Paragon⁠—Ship every SaaS integration your customers want — Find the transcript at: — Where to find Seth Godin: • Blog: • LinkedIn: • Website: — In this episode, we cover: (⁠00:00⁠) Seth’s background (⁠05:17⁠) Understanding good taste and upholding high standards (⁠08:09⁠) Become the best at whatever you do (⁠09:48⁠) Seth’s journey as a product manager (⁠14:09⁠) What people often get wrong when building products (⁠16:00⁠) Building a brand in the age of AI (⁠19:04⁠) Using AI to enhance writing (⁠22:40⁠) Four critical elements for an effective strategy (⁠27:38⁠) The role of tension in strategy (⁠29:15⁠) The concept of the purple cow (⁠33:11⁠) "Safe is risky" (⁠34:56⁠) The power of systems (⁠37:07⁠) Better waves make better surfers (⁠38:10⁠) Rebranding vs. re-logoing (⁠43:07⁠) Empathetic leadership (⁠44:14⁠) Conclusion and farewell — Referenced: • Seth Godin on the Tim Ferriss Show: • Persuasive communication and managing up | Wes Kao (Maven, Seth Godin, Section4): • Spinnaker: • Ray Bradbury: • Arthur C. Clarke: • Isaac Asimov: • Roger Zelazny: • Herbie Hancock: • Fahrenheit 451 (game): • RTFM: • Intercom: • Claude: • ChatGPT: • Anthropic: • Steam: • P.F. Flyer...

2024-12-08•45mins
#42

How a great founder becomes a great CEO | Jonathan Lowenhar (co-founder of Enjoy The Work)

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: the magic box paradigm • How to find and hire the best people • How to build a repeatable GTM machine • Why founders need to trust their intuition • Much more — Brought to you by: • ⁠Pendo⁠—The only all-in-one product experience platform for any type of application • ⁠OneSchema⁠—Import CSV data 10x faster • ⁠Vanta⁠—Automate compliance. Simplify security — Find the transcript at: — Where to find Jonathan Lowenhar: • X: • LinkedIn: • Enjoy the Work: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Jonathan’s background (02:56) Understanding the rhythm of well-run companies (09:20) The founder mode vs. manager mode debate (12:05) Common company failure modes (13:36) Common CEO failure modes (25:25) The magic box paradigm for selling your startup (43:07) Advice for founders on building relationships (49:28) Hiring and building an amazing team (57:11) Types of executives: architect, optimizer, scaler (59:45) Working backward in hiring (01:02:54) Four key components of a go-to-market strategy (01:15:01) Trusting founder intuition (01:19:12) Founder vs. CEO: different roles, different skills (01:20:52) Closing thoughts and lightning round — Referenced: • Founder mode memes: • Founder mode: • “Founder Mode” Is a Dangerous Red Herring: • Magic Box Paradigm: A Framework for Startup Acquisitions: • Facebook Buys Instagram for $1 Billion: • Chris Voss on X: • Who: • Brian Chesky on LinkedIn: • Joe Gebbia on LinkedIn: • Nathan Blecharczyk on ...

2024-12-05•1hr 34mins
#43

Identify your bullseye customer in one day | Michael Margolis (UX Research Partner at Google Ventures)

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 discuss: • ⁠⁠The step-by-step process of running a bullseye customer sprint • ⁠⁠The most common mistakes founders make when picking their first customers • ⁠⁠Practical tips for conducting effective customer interviews • ⁠⁠How to create simple but effective prototypes for user research • The power of “watch parties” in aligning teams around customer insights • How to apply these methods beyond typical tech startups — Brought to you by: • ⁠Eppo⁠—Run reliable, impactful experiments • ⁠Paragon⁠—Ship every SaaS integration your customers want • ⁠Enterpret⁠—Transform customer feedback into product growth — Find the transcript at: — Where to find Michael Margolis: • X: • LinkedIn: • Website: • Medium: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Michael’s background (09:11) Bullseye customers vs. ideal customer profiles (ICPs) (12:32) An overview of the bullseye customer sprint (20:56) When to use the bullseye customer sprint (22:19) Step one: Agree on goals and key questions (23:48) Step two: Define your bullseye customer (25:52) The importance of a narrow target audience (29:00) An example of step two in action (38:24) Narrowing attributes and exclusion criteria (43:28) Step three: Recruiting and compensating participants (56:11) Step four: Creating effective prototypes (01:01:10) Step five: Drafting your interview guide (01:08:49) Step six: The watch party method (01:19:40) Common pitfalls and final thoughts (01:24:43) Closing thoughts an...

2024-12-01•1hr 29mins
#44

The ultimate guide to founder-led sales | Jen Abel (co-founder of JJELLYFISH)

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 maintain momentum• Strategies for navigating procurement and closing deals• Common pitfalls in the sales process and how to avoid them—Brought to you by:• ⁠Brave Search⁠—A smarter way to search• ⁠Vanta⁠—Automate compliance. Simplify security• ⁠Paragon⁠—Ship every SaaS integration your customers want—Find the transcript at: to find Jen Abel:• X: LinkedIn: to find Lenny:• Newsletter: X: LinkedIn: this episode, we cover:(00:00) Jen’s background(02:20) The importance of founder-led sales(08:24) The steps of a sales cycle(12:01) Tactics for effective cold outreach(16:47) Conversion rate vs. win rate(20:20) The time it takes to find product-market fit(23:06) Identifying and engaging prospects(30:58) Nailing the first phone call(34:14) Buying vs. selling(38:08) Testing the questions to ask(41:57) Avoiding common sales questions and securing the second call(43:08) Co-authoring with customers(45:06) Time-boxing service contracts(49:20) Why you should avoid demos on the first call(51:05) Dealing with procurement(54:22) The power of enterprise sales(58:14) Getting a signature (01:00:15) Choosing a focus and overcoming sales challenges(01:02:19) General timelines(01:04:27) Final thoughts and advice(01:13:32) Working with Jen—Referenced:• Wiz: JJELLYFISH: Clay: A guide for finding product-market fit in B2B: Airtable: Figma: GitHub: Vanta: Christine Cacioppo on LinkedIn: Glengarry Glen Ross: A step-by-step guide to crafting a sales pitch that wins | April Dunford (author of Obviously Awesome ...

2024-11-24•1hr 16mins
#45

Behind the product: Replit | Amjad Masad (co-founder and CEO)

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, Amjad shares: • A live demo of Replit in action • How Replit’s AI agent can build full-stack web applications from a simple text prompt • The implications of AI-powered development for product managers, designers, and engineers • How this might reshape companies and careers • Why being “generative” will become an increasingly valuable skill • “Amjad’s law” and how learning to debug AI-generated code is becoming ever more valuable • Much more — Brought to you by: • ⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs • ⁠Persona⁠—A global leader in digital identity verification • ⁠LinkedIn Ads⁠—Reach professionals and drive results for your business — Find the transcript at: — Where to find Amjad Masad: • X: • LinkedIn: • Website: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Introduction to Amjad Masad and Replit (02:41) The vision and challenges of Replit (06:50) Replit’s growth and user stories (10:49) Demo of Replit’s capabilities (16:51) Building and iterating with Replit (25:04) Real-world applications and use cases (30:13) The technology stack (33:48) The evolution of Replit and its capabilities (39:36) The future of AI in software development (44:04) Skills for the future: generative thinking and coding (47:26) Amjad’s law (50:36) Replit’s new developments and future plans — Referenced: • Replit: • Cursor: • Aman Mathur on LinkedIn: • Node: • Claude: • Salesforce: • Wasm: • Figma: • Codecademy: • Hac...

2024-11-21•1hr 4mins
#46

Building Wiz: the fastest-growing startup in history | Raaz Herzberg (CMO and VP Product Strategy)

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 Sentinel. In our conversation, we discuss: • How Wiz pivoted from their initial idea and found deep product-market fit • What Raaz learned about listening to customers • Why she moved from product to marketing, despite no prior experience • How she thinks differently as a marketer with a product background • Lessons learned from scaling a hypergrowth startup like Wiz • Much more — Brought to you by: • ⁠WorkOS⁠—Modern identity platform for B2B SaaS, free up to 1 million MAUs • ⁠Rippling⁠—Automate HR, IT, and finance so you can scale faster • ⁠Cloudinary⁠—The foundational technology for all images and video on the internet — Find the transcript at: — Where to find Raaz Herzberg: • X: • LinkedIn: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Raaz’s background (02:54) Early challenges and Wiz’s essential pivot (06:41) Finding product-market fit (11:31) Lessons from early customer interactions (14:54) The power in speaking up when you don’t understand something (17:46) How Wiz pivoted from their initial idea (23:52) Marketing and leadership insights (28:05) Following the “heat” in your organization (30:22) How Raaz found success as CMO (34:01) Common CMO mistakes (36:23) Creating noise and standing out (40:28) Embracing failure and taking risks (44:53) The importance of clear communication (48:32) The “dummy” explanation (51:00) Building trust and company culture (53:45) Contrarian corner (56:34) Lightning round — Referenced: • Wiz: • An in...

2024-11-17•1hr 5mins
#47

Becoming an AI PM | Aman Khan (Arize AI, ex-Spotify, Apple, Cruise)

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 as an individual-contributor PM • Common pitfalls to avoid when building AI products • The importance of energy and curiosity in product roles • Much more — Brought to you by: • ⁠⁠Pendo⁠⁠—The only all-in-one product experience platform for any type of application • ⁠⁠Vanta⁠⁠—Automate compliance. Simplify security • ⁠⁠Paragon⁠⁠—Ship every SaaS integration your customers want — Find the transcript at: ⁠ — Where to find Aman Khan: • X: ⁠ • LinkedIn: ⁠ • Website: ⁠ — Where to find Lenny: • Newsletter: ⁠ • X: ⁠ • LinkedIn: ⁠ — In this episode, we cover: (00:00) Aman’s background (06:16) Understanding AI product management roles (13:29) Getting started as an AI product manager (18:14) Building a portfolio and standing out (22:31) Why product management is not dead (28:56) How to thrive as an AI product manager (35:42) Finding good ideas that are AI-oriented (39:27) Be careful not to automate away every customer experience (42:53) What separates top 5% AI PMs (46:55) Key habits for long-term IC success (52:48) The importance of energy in meetings (57:00) Wandering vs. waiting (01:01:41) Amplifying signal through AI tools (01:03:18) Just have fun (01:05:36) Lightning round — Referenced: • AI Resources and Tools for PMs (Updated Oct 2024): ⁠ • Unlocking the AI PM Dream: Your Roadmap to Success: ⁠ • Arize: ⁠ • Ryzen: ⁠ • NotebookLM: ⁠ • Figma: ⁠ • Cursor: ⁠ • Replit: ⁠ • Excalidraw: ⁠ • Vercel: ⁠ • v0: ⁠ • How Airbnb Proved That Storytelling Is the Most Important Skill in Design: ⁠...

2024-11-14•1hr 17mins
#48

Everything you’ve ever wanted to know about SAFe and the product owner role | Melissa Perri (author, founder of Product Institute)

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 with the SAFe framework • How large non-tech companies can improve their product practices • Much more — Brought to you by: • ⁠Pendo⁠—The only all-in-one product experience platform for any type of application • ⁠OneSchema⁠—Import CSV data 10x faster • ⁠Coda⁠—The all-in-one collaborative workspace — Find the transcript at: — Where to find Melissa Perri: • X: • LinkedIn: • Website: • Product Institute: • Podcast: — Where to find Lenny: • Newsletter: • X: • LinkedIn: — In this episode, we cover: (00:00) Melissa’s background (02:12) The rise of the product owner role (06:37) Understanding Agile and Scrum (08:27) Challenges in Agile transformations (10:41) The history of the product owner role (13:58) The Scrum Guide (15:43) Product owner responsibilities (21:01) Adopting Scrum in organizations (26:21) The origins and implementation of SAFe (35:20) Why Melissa doesn’t recommend SAFe (40:33) Advice for implementing a digital transformation (49:12) An example of SAFe adoption (51:27) The value of experienced product leaders (56:53) Career paths for product owners (01:04:14) Transitioning from product owner to product manager (01:06:41) Be careful relying on certifications (01:11:43) Evaluating existing product owners (01:16:55) Final thoughts on Agile and product management — Referenced: • Escaping the Build Trap: How Effective Product Management Creates Real Value: • Lean UX: • Scrum: • What is Extreme Programming? • Capital One: • The Agile Manifesto: • Ken Schwaber on X: • Je...

2024-11-10•1hr 24mins
#49

Breaking the rules of growth: Why Shopify bans KPIs, optimizes for churn, prioritizes intuition, and builds toward a 100-year vision | Archie Abrams (VP Product, Head of Growth at Shopify)

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 Shopify optimizes for churn • Why the core product team doesn’t use metrics-based goals • Why they keep multi-year experiment holdouts • How they structure their growth team • The benefits of not having a CMO • Lessons learned about integrating sales into a product-led growth model • The power of discounting as a growth lever • Much more — Brought to you by: • ⁠⁠Explo⁠⁠—Embed customer-facing analytics in your product • ⁠⁠Dovetail⁠⁠—The customer insights hub for product teams — Find the transcript at: ⁠ — Where to find Archie Abrams: • X: ⁠ • LinkedIn: ⁠ — Where to find Lenny: • Newsletter: ⁠ • X: ⁠ • LinkedIn: ⁠ — In this episode, we cover: (00:00) Archie’s background (02:30) Shopify’s impressive growth (06:17) Shopify’s unique approach to churn and retention (08:43) Monetization model and success metrics (11:08) Long-term experimentation and metrics (23:00) Examples of big wins that Archie’s team has shipped (26:42) Monetary friction (27:14) Metrics (29:47) Shopify’s growth team structure (33:03) Goal setting and forecasting (37:10) Examples of long-term results within Shopify (41:36) Shipping neutral experiments (42:05) Building a hundred-year company (48:04) Why Shopify doesn’t use KPIs (51:30) Shopify’s “Get shit done” framework (54:30) Cross-team collaboration (58:48) The importance of an opinionated founder (01:01:12) Growth and sales integration (01:06:42) Shopify’s marketing structure (01:08:49) Insights on discounting from Udemy (01:11:09) Lightning round — Referen...

2024-11-07•1hr 17mins

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