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1:41:44ENZig When Others Zag: HubSpot Co-founder Dharmesh Shah on Simplicity, Culture as a Product and Building a Company Around Your StrengthsGuest Dharmesh Shah · Host Lenny RachitskyThe HubSpot co-founder and CTO explains why he has never had a direct report, how he measures laughs per minute, and the first-principles habits behind HubSpot's contrarian choices.
1:02:49ENStop Being the Arrogant Doctor: Andy Raskin on Pitching a Movement, Not a ProductGuest Andy Raskin · Host Lenny RachitskyStrategic narrative consultant Andy Raskin explains the five-part story structure behind pitches at Salesforce, Zuora and Gong, and how to make it your company's north star.
1:10:32ENA Billion Dollars, No VC, Under 100 People: Surge AI's Edwin Chen on Data Quality and Where AI Is HeadingGuest Edwin Chen · Host Lenny RachitskySurge AI's founder explains how a bootstrapped team built the leading human-data company, why he distrusts benchmarks, and how reinforcement learning environments are the next frontier.
1:16:17ENFaster, But for What? Nicole Forsgren on Measuring Developer Productivity in the AI EraGuest Nicole Forsgren · Host Lenny RachitskyThe creator of DORA and SPACE explains why most productivity metrics mislead, how AI changes flow and trust, and how to build a developer experience program that proves its value.
1:04:21ENOnboarding Is Growth's Biggest Lever: Lessons from Airtable's Former Head of GrowthGuest Lauryn Isford · Host Lenny RachitskyLauryn Isford on rethinking experimentation, choosing a hard-to-reach activation metric, reverse trials, and the PLG funnel.
1:49:39ENNo Investors, 24 Profitable Years: Jason Fried on Staying Small, Trusting Your Gut and Making Money FirstGuest Jason Fried · Host Lenny RachitskyThe 37signals co-founder explains how a 75-person, investor-free company has out-earned far larger rivals, and why he builds products in two-person, six-week cycles.
1:34:57ENFifteen People, Four Products, Zero Handwritten Code: Inside Every's AI-First CompanyGuest Dan Shipper · Host Lenny RachitskyEvery CEO Dan Shipper explains how his small team uses Claude Code, an AI operations lead and compounding engineering to do the work of a much larger company.
1:36:24ENBe a Willow Tree: Julie Zhuo on Managing Agents, Teams of Builders, and Data That DiagnosesGuest Julie Zhuo · Host Lenny RachitskyThe former Facebook head of design and Sundial founder explains how management skills carry over to AI tools, why she hires no product managers, and what new managers still get wrong.
1:54:03ENStarving on Purpose: What Atlassian Learned About Building New Products Inside a GiantGuest Tanguy Crusson · Host Lenny RachitskyTanguy Crusson walks through HipChat, Statuspage and Jira Product Discovery to explain why zero-to-one is so hard in a large company and how Atlassian's Point A incubator made room for it.
1:01:41ENDon't Outsource the Learning: Pete Kazanjy's Case for Founder-Led SalesGuest Pete Kazanjy · Host Lenny RachitskyThe author of Founding Sales explains why B2B founders should sell for a long time themselves, how to know when to hire, and how to get better at selling.
1:29:12ENThe Next Distribution Platform Is Coming, and ChatGPT Is the Likeliest HostGuest Brian Balfour · Host Lenny RachitskyReforge founder Brian Balfour lays out the four-step cycle every distribution platform follows, why he expects ChatGPT to open the next one, and how startups and incumbents should bet.
1:23:43ENScripts for the Hard Stuff: How an Executive Coach Handles Feedback, Firing and Founder FightsGuest Alisa Cohn · Host Lenny RachitskyAlisa Cohn walks through word-for-word scripts for difficult workplace conversations, a three-question meeting close, and a founder "prenup" of questions to settle before you start a company.
1:07:36ENHow Notion Built a Community That Sold Its Product for ItGuest Camille Ricketts · Host Lenny RachitskyCamille Ricketts, Notion's first marketing hire, explains how community-led growth and content marketing actually work in practice.
1:11:08ENFear Gives Bad Advice: An Executive Coach's Playbook for Firing, Layoffs and FocusGuest Matt Mochary · Host Lenny RachitskyExecutive coach Matt Mochary tells Lenny Rachitsky how he helps CEOs act through fear, let people go humanely, run layoffs, innovate inside big companies and audit their energy.
1:05:00ENFrom Arctic Code Vault to Autocomplete: How GitHub Copilot Went From Moonshot to ProductGuest Ryan J. Salva · Host Lenny RachitskyGitHub VP of product Ryan J. Salva explains how a small research team's experiment became Copilot, and what it took to scale it responsibly.
1:09:35ENKill Your Own Project, Diversify Your Growth: Noam Lovinsky's Lessons from YouTube, Thumbtack, Facebook and GrammarlyGuest Noam Lovinsky · Host Lenny RachitskyGrammarly's chief product officer walks through four very different chapters of his career and the principles each one taught him.
1:27:45ENFast Beats Right: Claire Vo on the CPTO Role, Moving Like a Startup and What AI Will Take From PMsGuest Claire Vo · Host Lenny RachitskyLaunchDarkly's chief product officer and ChatPRD creator shares career advice, her playbook for pace and standards, and a view on which product skills AI will replace.
1:16:57ENHow Ramp Reached $100M in Revenue with 50 People: Velocity, Single-Threaded Teams and Context Over ControlGuest Geoff Charles · Host Lenny RachitskyRamp's VP of Product Geoff Charles explains to Lenny Rachitsky how a culture of velocity, tiny focused teams and radically empowered engineers drove one of the fastest SaaS growth runs on record.
1:12:52ENFrom Google+ to the Tabbed Inbox: How to Build Products on Evidence, Not OpinionGuest Itamar Gilad · Host Lenny RachitskyFormer Google product manager Itamar Gilad contrasts a failed social network with a hit Gmail feature and walks through the GIST framework from his book Evidence-Guided.
1:42:21ENCommunication Is the Job: Meta CTO Andrew "Boz" Bosworth on 18 Years from Facebook's Early Days to Reality LabsGuest Andrew "Boz" Bosworth · Host Lenny RachitskyBosworth recounts the unglamorous early days of Facebook, the building of News Feed, and the leadership lessons he drew from managing up, communicating clearly and learning to be curious instead of defensive.
1:28:32ENInside Duolingo's Streak: What 600+ Experiments Taught One Retention TeamGuest Jackson Shuttleworth · Host Lenny RachitskyDuolingo group product manager Jackson Shuttleworth walks through the history, wins, wrong turns and operating habits behind the single feature he calls the company's biggest growth lever.
1:26:32ENThe Achiever's Trap: A Growth Leader on Burnout, Healing and Letting the Old Self GoGuest Andy Johns · Host Lenny RachitskyFormer Facebook, Twitter and Wealthfront growth leader Andy Johns explains how achievement became his survival strategy, why it broke down, and the four steps he sees in deep personal change.
1:17:24ENDon't Plan Your Career, Follow the Best People: Tamar Yehoshua on Product Leadership in the AI EraGuest Tamar Yehoshua · Host Lenny RachitskyGlean's president of product and technology on career choices, what she learned from Bezos, Butterfield and Benioff, working with engineering partners, and how AI will change product work.
1:25:36ENMake Things People Want: What 600 YC Startups Taught Gustaf AlströmerGuest Gustaf Alstromer · Host Lenny RachitskyA Y Combinator group partner and early Airbnb growth lead explains why startups fail, what successful founders share, and why climate tech has become a real business.
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