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1:47:31ENFrom Fever Dream to Wilderness: Drew Houston on Dropbox's Three ErasGast: Drew Houston · Moderation: Lenny RachitskyDropbox's co-founder and CEO gives a candid account of explosive growth, the Google Photos shock, a painful pivot to productivity, and the personal and organizational reset that followed.
34:57ENIt's Six Months In: Misconceptions About AI, Regulation, Context Windows and IncumbentsModeration: Sarah Guo, Elad GilSarah Guo and Elad Gil answer listener questions on what the market gets wrong about generative AI, from the nuclear-regulation analogy to where startups can still beat incumbents.
2:01:57ENBuild the Sales Team Like a Founder: Jason Lemkin on Hiring, Comp and Keeping Product CloseGast: Jason Lemkin · Moderation: Lenny RachitskySaaStr founder Jason Lemkin walks through when to hire your first reps, who to hire, how to pay them, how product and sales should work together, and why customer-hostile tactics don't compound.
1:02:49ENStop Being the Arrogant Doctor: Andy Raskin on Pitching a Movement, Not a ProductGast: Andy Raskin · Moderation: 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.
44:30ENOpen the Front Door: Emil Michael on Rebuilding U.S. Defense Around Startups, AI and Supply ChainsModeration: Sarah Guo, Elad GilThe Pentagon's research and engineering chief explains his six technology priorities, the rapid launch of GenAI.mil, and why new entrants and domestic manufacturing are now urgent.
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.
1:29:12ENThe Next Distribution Platform Is Coming, and ChatGPT Is the Likeliest HostGast: Brian Balfour · Moderation: 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.
56:39ENDeals Don’t Die From Competition—They Die From IndecisionModeration: Lenny RachitskyMatt Dixon distills 2.5 million sales conversations into the JOLT method for frozen buyers and the Challenger lesson on teaching insight.
1:16:09ENFrom Free Users to Enterprise Contracts: The Product-Led Sales PlaybookModeration: Lenny RachitskyElena Verna explains how product-led sales turns self-serve usage into enterprise pipeline, and what product, sales, marketing, data, and tooling must change to make it work.
1:07:36ENHow Notion Built a Community That Sold Its Product for ItGast: Camille Ricketts · Moderation: Lenny RachitskyCamille Ricketts, Notion's first marketing hire, explains how community-led growth and content marketing actually work in practice.
1:55:10ENSEO After AI Overviews: Treat Search as a Product, Not a Keyword GameGast: Eli Schwartz · Moderation: Lenny RachitskyGrowth advisor Eli Schwartz explains how AI answers are swallowing top-of-funnel search, and why the winners will be the teams that build for the buyer's journey.
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.
1:24:36ENThe Wrong Maths of Marketing: Rory Sutherland on Why Great Products Need Psychology, Timing, and FameModeration: Lenny RachitskyOgilvy's Rory Sutherland explains why rational product logic fails, how idiosyncrasy and timing shape adoption, and why brand fame compounds non-linearly.
1:20:12ENThe 10X Growth Advisor: Impact, Hiring, SEO and the End of Search as We Know ItGast: Luc Levesque · Moderation: 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.
1:31:26ENMake 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.
59:19ENThe Layering Game: Elena Verna on Product-Led Growth, Product-Led Sales, and Smarter FreemiumModeration: Lenny RachitskyA growth strategist explains how B2B companies should sequence product-led and sales-led motions without crushing the user engine that created them.
1:21:13ENBad Friction, Good Friction: Laura Schaffer on User Psychology and Growth ExperimentsGast: Laura Schaffer · Moderation: Lenny RachitskyThe new head of growth at Amplitude explains how she built a growth team at Twilio, why most experiments fail, and why the user's state of mind decides what converts.
1:16:16ENSharp Problems, Real Virality: Oji Udezue's Playbook for Product-Led GrowthGast: Oji Udezue · Moderation: Lenny RachitskyTypeform's chief product officer draws on Microsoft, Atlassian, Calendly and Twitter to explain how to pick a problem, find your ICP, onboard users and earn word of mouth.
1:31:24ENEvery Problem Is Our Problem: How HubSpot's Chris Miller Grew a PLG Engine and HimselfGast: Chris Miller · Moderation: Lenny RachitskyHubSpot's VP of Product for Growth and AI on the traits of great growth PMs, the myths of product-led growth, and how HubSpot's flywheel really works.
1:26:02ENGo-to-Market as a Product: Inside Vercel's Agent-Powered Sales MachineGast: Jeanne DeWitt Grosser · Moderation: 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 ConclusivelyGast: Sri Batchu · Moderation: 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 ScaleGast: Geoffrey Moore · Moderation: 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.
1:14:03ENThere Is No Marketing Playbook: Krithika Shankarraman's DATE FrameworkGast: Krithika Shankarraman · Moderation: Lenny RachitskyThe first marketing hire at OpenAI and Stripe explains why diagnosing your own problem beats copying other companies' tactics.
54:05ENServal's Jake Stout on Outbuilding ServiceNow: Mirror the System of Record, Bet on Code, and Ship Before the Incumbent Can Book a MeetingModeration: Jacob EffronHow an AI-native employee-support startup attacks a legacy ITSM incumbent with velocity, code-generated workflows and a permissions-first architecture.
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