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1:42:04ENPaid Growth, Step by Step: Shopify's Performance Marketing Lead on Tests, Signal and Team DesignGuest Timothy Davis · Host Lenny RachitskyTimothy Davis walks through when to start paid, how to run signs-of-life tests, which platforms to try, what to measure and who to hire first.
1:00:51ENInflict Pain, But Do It With a Smile: Julia Schottenstein on dbt's Rise and the Art of Getting AcquiredGuest Julia Schottenstein · Host Lenny RachitskyA former NEA investor turned dbt Cloud product leader explains why dbt won, how to approach M&A and pricing, and how venture habits make her a better PM.
1:22:03ENWin Where Rivals Say "Life's Too Short": Roger Martin on the Five Questions of StrategyGuest Roger Martin · Host Lenny RachitskyThe Playing to Win author walks through his strategy choice cascade, explains why differentiation or low cost is non-negotiable, and shows how to start fixing strategy one gap at a time.
2:14:15ENEric Ries on the Lean Startup After 12 Years: What MVPs Really Mean, When to Pivot, and Building Companies for Human FlourishingGuest Eric Ries · Host Lenny RachitskyThe author of The Lean Startup revisits misconceptions about MVPs and pivots, offers advice for stuck founders, and argues that governance, not just product, decides whether companies do good.
53:17ENCharge Sooner, Price Higher, Never Set It and Forget It: Naomi Ionita on MonetizationGuest Naomi Ionita · Host Lenny RachitskyMenlo Ventures partner and former Evernote growth leader Naomi Ionita explains when to start charging, how to set and evolve prices, and what a "modern growth stack" looks like.
1:05:20ENPolite Interest Is Not Demand: How Wiz Found Product-Market Fit, and Then Made Some NoiseGuest Raaz Herzberg · Host Lenny RachitskyRaaz Herzberg, Wiz's CMO and VP of product strategy, tells how the company's early pivot worked, why she moved from product into marketing, and what she learned along the way.
55:51ENHumble, Customer-Obsessed and Relentless: Inside DoorDash's CultureGuest Keith Yandell · Host Lenny RachitskyDoorDash executive Keith Yandell explains how the company hires for culture, leads through crises, and manages people, from WeDash deliveries to a "how to work with me" document.
57:19ENMarc Benioff on Beginner's Mind, Agentforce and Staying a Startup After 25 YearsGuest Marc Benioff · Host Lenny RachitskyThe Salesforce co-founder talks Steve Jobs, a legendary launch stunt, what an AI agent actually is, and how he leads through reinvention.
1:21:01ENMake It Explicit: Annie Duke on Deciding Better and Quitting SoonerGuest Annie Duke · Host Lenny RachitskyFormer poker champion Annie Duke explains how independent input, shorter feedback loops, pre-mortems with kill criteria and a willingness to quit improve decisions at companies and in life.
1:36:49ENMission, Retention and an Owl With Attitude: How Duolingo Grew From 3 Million to 200 Million Users Without Paid AdsGuest Gina Gotthilf · Host Lenny RachitskyFormer Duolingo growth lead Gina Gotthilf on organic growth, brand voice, her career B-sides, and why she is betting on Latin American startups.
1:34:36ENFounder Is an Attitude, CEO Is a Craft: Jonathan Lowenhar on Failure Modes, Magic Box Exits and HiringGuest Jonathan Lowenhar · Host Lenny RachitskyEnjoy The Work's Jonathan Lowenhar lays out the skills founders must learn to become CEOs, from avoiding common failure modes to selling a company, hiring, go-to-market and trusting intuition.
1:28:58ENBret Taylor on Failing Forward: From Google Local to Google Maps to Sierra's AgentsGuest Bret Taylor · Host Lenny RachitskyThe co-creator of Google Maps and FriendFeed's like button on career mindset, the future of coding, where AI startups should build, and why agents will bring outcome-based pricing.
1:26:31ENSelling in a Downturn: Bravado CEO Sahil Mansuri on Forecasts, Comp Plans, Retention and Warm IntrosGuest Sahil Mansuri · Host Lenny RachitskySahil Mansuri, founder of the sales community Bravado, lays out how B2B founders should change quotas, compensation, customer focus and deal-closing tactics when the market turns.
1:34:55ENInside $3.5 Billion of Paid Growth: Creative Testing, Attribution Humility and Channel DiversificationGuest Jonathan Becker · Host Lenny RachitskyJonathan Becker of Thrive Digital explains how performance marketing really works after the privacy shifts, and where creative, measurement and AI fit in.
1:40:04ENCompanies Are Equations: Tom Conrad on Pandora, Quibi and the Math Behind Product SuccessGuest Tom Conrad · Host Lenny RachitskyA veteran of Apple, Pandora, Snap, Pets.com and Quibi explains what hits and disasters taught him about choosing teams, business-model math, burnout and why not everyone should found a company.
1:48:35ENDon't Compete for the 24%: Christopher Lochhead on Designing and Dominating Your Own CategoryGuest Christopher Lochhead · Host Lenny RachitskyThe self-styled Godfather of Category Design explains why the "better" product usually loses, how to reframe a problem with new language, and how to launch with word of mouth.
1:20:53ENDon't Die: Y Combinator's Dalton Caldwell on Keeping a Startup AliveGuest Dalton Caldwell · Host Lenny RachitskyThe YC group partner on pivots, tarpit ideas, why investors say no, how to talk to customers, and what he hopes founders will build next.
1:23:46ENSurviving the Next Crisis: Waze Co-Founder Uri Levine on Cash Shocks, Lost Product-Market Fit and Never Giving UpGuest Uri Levine · Host Lenny RachitskyUri Levine explains how founders should diagnose a startup crisis, act within days, keep their teams on board and decide whether to pivot or shut down.
1:13:13ENOKRs Are a Vitamin, Not a Medicine: Christina Wodtke on Making Goals Actually WorkGuest Christina Wodtke · Host Lenny RachitskyThe Stanford lecturer and author of Radical Focus explains what OKRs are really for, why they fail, and how to run a healthy weekly cadence.
1:33:55ENGetting Startup Press Without a Rolodex: A Practical PR PlaybookGuest Emilie Gerber · Host Lenny RachitskyPR agency founder Emilie Gerber walks through which outlets to target, how to write a three-sentence pitch, and how to judge whether press is worth the effort.
1:11:56ENHow to Get ChatGPT to Recommend Your Product: A Practical Guide to Answer Engine OptimizationGuest Ethan Smith · Host Lenny RachitskyGraphite CEO Ethan Smith explains how AEO differs from SEO, which levers move the needle, and how to measure and test what works.
1:08:08ENCastle or Shack? Hamilton Helmer on Which Business Advantages Actually LastGuest Hamilton Helmer · Host Lenny RachitskyThe author of 7 Powers explains how to tell real, durable competitive power from things that merely feel like an advantage, and when founders should start looking for it.
1:24:56ENThe Social Radar: How Jessica Livingston Read Founders in Ten-Minute InterviewsGuest Jessica Livingston · Host Lenny RachitskyThe Y Combinator co-founder explains what she looked for in early-stage founders, the Airbnb interview she never forgot, and why she started her own podcast.
1:10:54ENFuel and Engine: A Practical Playbook for Hiring Your First B2B MarketerGuest Emily Kramer · Host Lenny RachitskyMarketing leader and investor Emily Kramer explains how to diagnose what your startup's marketing needs, who to hire, and how product and marketing teams can work well together.
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