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1:27:13ENFour Levels of Product-Market Fit: First Round's Playbook for B2B FoundersGast: Todd Jackson · Moderation: Lenny RachitskyTodd Jackson of First Round Capital walks through a staged framework for finding product-market fit, the benchmarks for each stage, and the four Ps you can change when you're stuck.
1:21:25ENStrategy Before Goals: Ravi Mehta's Product Strategy Stack, Tinder Lessons and Selective MicromanagementGast: Ravi Mehta · Moderation: Lenny RachitskyFormer Tinder CPO Ravi Mehta on how startups differ from big companies, how to layer mission, strategy, roadmap and goals, and how product leaders can grow.
55:51ENHumble, Customer-Obsessed and Relentless: Inside DoorDash's CultureGast: Keith Yandell · Moderation: 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.
1:21:48ENSeeing Like a Designer: Jessica Hische on Logos, Brands and Knowing When Good Enough Is EnoughGast: Jessica Hische · Moderation: Lenny RachitskyLettering artist Jessica Hische walks through her refresh of Lenny's logo and explains how founders can read type, time a rebrand and avoid overspending on brand.
1:36:49ENMission, Retention and an Owl With Attitude: How Duolingo Grew From 3 Million to 200 Million Users Without Paid AdsGast: Gina Gotthilf · Moderation: 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 HiringGast: Jonathan Lowenhar · Moderation: 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.
1:26:31ENSelling in a Downturn: Bravado CEO Sahil Mansuri on Forecasts, Comp Plans, Retention and Warm IntrosGast: Sahil Mansuri · Moderation: 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.
1:48:35ENDon't Compete for the 24%: Christopher Lochhead on Designing and Dominating Your Own CategoryGast: Christopher Lochhead · Moderation: 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.
1:22:34ENName It, Position It, Give It a Personality: A Startup Brand Playbook from Gmail and Square Veteran Arielle JacksonGast: Arielle Jackson · Moderation: Lenny RachitskyArielle Jackson explains how early-stage founders should pick a name, define purpose, positioning and personality, land press coverage, and know when to hire a marketer.
1:20:53ENDon't Die: Y Combinator's Dalton Caldwell on Keeping a Startup AliveGast: Dalton Caldwell · Moderation: 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 UpGast: Uri Levine · Moderation: 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.
1:17:35ENStick With It: Chris Hutchins on Big Product Bets and Building a Top Business PodcastGast: Chris Hutchins · Moderation: Lenny RachitskyThe former Wealthfront product lead behind All the Hacks explains how to run bold bets inside a company and how to launch, grow and sustain a podcast.
1:33:55ENGetting Startup Press Without a Rolodex: A Practical PR PlaybookGast: Emilie Gerber · Moderation: 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.
1:24:56ENThe Social Radar: How Jessica Livingston Read Founders in Ten-Minute InterviewsGast: Jessica Livingston · Moderation: 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 MarketerGast: Emily Kramer · Moderation: 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.
1:41:44ENZig When Others Zag: HubSpot Co-founder Dharmesh Shah on Simplicity, Culture as a Product and Building a Company Around Your StrengthsGast: Dharmesh Shah · Moderation: 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.
1:49:39ENNo Investors, 24 Profitable Years: Jason Fried on Staying Small, Trusting Your Gut and Making Money FirstGast: Jason Fried · Moderation: 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.
1:01:41ENDon't Outsource the Learning: Pete Kazanjy's Case for Founder-Led SalesGast: Pete Kazanjy · Moderation: 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.
1:16:57ENHow Ramp Reached $100M in Revenue with 50 People: Velocity, Single-Threaded Teams and Context Over ControlGast: Geoff Charles · Moderation: 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.
1:25:36ENMake Things People Want: What 600 YC Startups Taught Gustaf AlströmerGast: Gustaf Alstromer · Moderation: 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.
1:24:57ENSelling the Opportunity: How Founders Take Enterprise Sales From $1M to $10M ARRGast: Jen Abel · Moderation: 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.
1:44:26ENFind the Must-Have Users First: Sean Ellis on Product-Market Fit and Sustainable GrowthGast: Sean Ellis · Moderation: Lenny RachitskyThe creator of the Sean Ellis test and the ICE framework explains how to measure product-market fit, learn from the users who love you, and then grow in the right order.
1:31:26ENMake Individual Contributors Love You First: Inside Figma's Bottom-Up Growth PlaybookGast: Claire Butler · Moderation: 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.
1:42:28ENJournalists Don't Care About You: A Magazine Editor's Field Guide to Getting PressGast: Jason Feifer · Moderation: Lenny RachitskyEntrepreneur editor-in-chief Jason Feifer explains how to prepare, pick the right writer, and pitch a story that an editor will actually say yes to.
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