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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.
1:37:19ENImpact, Inquiry and Letting Fires Burn: Vlad Loktev's Playbook from a Decade Inside AirbnbHost Lenny RachitskyFormer Airbnb homes GM and new Index Ventures partner Vlad Loktev tells Lenny Rachitsky how he prioritizes, disagrees, scales teams and keeps his balance in hypergrowth.
1:24:24ENIntelligence for Heavy Machines: Qasar Younis on Why Physical AI Will Change Farms, Mines and Roads FirstHost Lenny RachitskyThe Applied Intuition co-founder explains why the biggest near-term AI impact is in vehicles and industrial machines, and shares the values, reading habits and management philosophy behind a quiet $15 billion company.
1:36:29ENSmiling Exhaustion: Inside the Tech Worker Sentiment Survey as AI's Honeymoon FadesHost Lenny RachitskyNoam Segal and Lenny Rachitsky walk through the second annual Tech Worker Sentiment Survey, which captured about 6,000 people in tech and found a workforce split down the middle by AI.
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.
1:25:36ENMake 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.
1:42:00ENThe Operating Lessons Brian Balfour Keeps Returning ToHost Lenny RachitskyReforge’s founder and CEO shares hard-won lessons on hiring, planning, growth systems, and defining who you are not for.
1:16:53ENEngineering Leadership After ZIRP: Strategy, Systems and AccountabilityGuest Will Larson · Host Lenny RachitskyCarta CTO Will Larson on how engineering management changed after the zero-interest-rate era, and the habits he relies on now: systems models, written strategy, shared incentives and honest values.
1:24:57ENSelling the Opportunity: How Founders Take Enterprise Sales From $1M to $10M ARRGuest Jen Abel · Host Lenny RachitskyJen Abel explains why startups should chase tier-one logos, price near $100K, hire salespeople who can "cosplay a founder", and sell vision instead of problems.
1:08:07ENContext Is All You Need: Inside OpenAI with Logan KilpatrickGuest Logan Kilpatrick · Host Lenny RachitskyOpenAI's head of developer relations on GPTs, prompting, how the company ships fast, and where startups can build without being steamrolled.
1:20:12ENThe 10X Growth Advisor: Impact, Hiring, SEO and the End of Search as We Know ItGuest Luc Levesque · Host Lenny RachitskyShopify's chief growth officer Luc Levesque explains how to hire and use growth advisors, why SEO can define a company, and what AI answers mean for search traffic.
1:47:22ENStrategy Is Not a Gift: A Five-Phase Playbook You Can Run in 8–12 WeeksGuest Chandra Janakiraman · Host Lenny RachitskyChandra Janakiraman, CPO of VRChat, walks through an operator's recipe for building product strategy, from leadership interviews to a three-pillar rollout, plus a longer "big S" process for aspirational futures.
1:28:28ENFish Where the Fish Are: Andrew Wilkinson on Boring Businesses, AI Agents and Why Money Didn't Make Him HappyGuest Andrew Wilkinson · Host Lenny RachitskyThe co-founder of Tiny, the "Berkshire Hathaway of the internet", explains how to pick a startup idea, how he runs his life on AI agents, and what actually changed his happiness.
1:17:46ENShopify’s Anti-Playbook: Optimize for Churn, Hold Experiments for Years, and Ban KPIsHost Lenny RachitskyArchie Abrams explains how Shopify grows by lowering barriers, measuring cohort GMV, running multi-year holdouts, and letting a 100-year vision guide core product.
1:31:26ENMake Individual Contributors Love You First: Inside Figma's Bottom-Up Growth PlaybookGuest Claire Butler · Host Lenny RachitskyClaire Butler, Figma's 10th employee and first marketer, explains the two-step go-to-market motion behind Figma's growth: win over individual contributors, then help them spread the product through their companies.
1:25:50ENThe Skip, the Sidecar, and the Rabbit You Should Never Catch: Nikhyl Singhal on Building a 60-Year Product CareerHost Lenny RachitskyMeta and former Credit Karma product leader Nikhyl Singhal explains how to plan a career backwards from the job after next, spot ex-growth companies, diagnose a stalled promotion, and survive the success you've been chasing.
1:33:28ENWorking Backwards: How Amazon Turned Customer Obsession into a Repeatable Operating SystemGuest Bill Carr · Host Lenny RachitskyFormer Amazon VP Bill Carr explains the PR/FAQ, single-threaded leaders, input metrics, disagree-and-commit and Bar Raisers, and how other companies can adopt them.
1:26:02ENGo-to-Market as a Product: Inside Vercel's Agent-Powered Sales MachineGuest Jeanne DeWitt Grosser · Host Lenny RachitskyVercel COO and former Stripe sales leader Jeanne DeWitt Grosser explains how go-to-market engineers, AI agents and product thinking are reshaping sales.
1:17:18ENInside Ramp's Growth Engine: Velocity, Payback Period and Failing ConclusivelyGuest Sri Batchu · Host Lenny RachitskyRamp's head of growth Sri Batchu explains how the fastest-growing SaaS company in history organizes its growth teams, picks metrics, runs experiments and hires.
1:24:50ENCrossing the Chasm, Explained by Its Author: Start Small, Win a Segment, Then ScaleGuest Geoffrey Moore · Host Lenny RachitskyGeoffrey Moore walks through the technology adoption lifecycle, the four go-to-market playbooks that fit each stage, and the mistakes that keep B2B startups stuck.
1:19:36ENWise and Curious: Chip Conley on Mentoring Brian Chesky, Dying Nine Times and Learning to Love MidlifeHost Lenny RachitskyThe hotelier who became Airbnb's "modern elder" at 52 on working for a founder in founder mode, why age diversity is a team asset, and what a near-death experience taught him.
1:23:01ENThe Meteor Is Coming: Intercom's Paul Adams on Going All In on AIGuest Paul Adams · Host Lenny RachitskyIntercom's chief product officer talks about the failures that shaped him, how Intercom ripped up its strategy after ChatGPT, and the simple frameworks he uses to decide what to build.
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