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58:30ENHe Couldn't Convince Anyone to Compete with OpenAI. Two Years Later the Valley Is Full of Them.Moderation: Nathan LabenzSarah Guo and Elad Gil walk Cognitive Revolution through Software 3.0, an 80/20 split with incumbents, and how to tell a fake waitlist from demand that cannot be faked.
59:06ENMark Goldberger on Enterprise Sales, Hiring and Deal QualificationGast: Mark Goldberger · Moderation: Harry StebbingsRamp’s enterprise sales leader discusses founder-led selling, champions, onboarding and building a disciplined pipeline.
1:01:46ENFrank Fillmann on Enterprise Sales, Hiring and Customer-Centered PlaybooksGast: Frank Fillmann · Moderation: Harry StebbingsThe Salesforce sales leader explains how he coaches teams, maps opportunities and builds a case around the buyer’s priorities.
1:03:41ENAdam Grenier on Building Growth into the BusinessGast: Adam Grenier · Moderation: Harry StebbingsThe former Uber growth leader explains marketplace acquisition, hiring, retention and the limits of attribution through lessons from Uber, Lambda School and MasterClass.
41:17ENZach Lawryk on Sales Engineering, Buyer Value and Building the First TeamGast: Zach Lawryk · Moderation: Harry StebbingsThe Rippling solutions consulting leader explains when to hire technical sales specialists, how to evaluate them and how they help buyers make decisions.
50:12ENThe Drone Is Only 15 Percent of the ProblemModeration: Sarah Guo, Elad GilZipline CEO Keller Rinaudo Cliffton on why blood delivery in Rwanda, not a cooler airplane, built the world's largest commercial autonomous system.
1:01:55ENMike Duboe on Growth Teams, Experiments and Paid MarketingGast: Mike Duboe · Moderation: Harry StebbingsThe former Stitch Fix growth leader explains how to choose meaningful metrics, hire for growth and test whether marketing actually creates demand.
1:00:17ENStevie Case on Building Sales Teams, Moving Upmarket and Leading With EmpathyGast: Stevie Case · Moderation: Harry StebbingsVanta CRO Stevie Case explains how founders can test enterprise sales, hire for grit and curiosity, and build a more human sales culture.
37:15ENJeff Jordan on Building Two-Sided MarketplacesGast: Jeff Jordan · Moderation: Harry StebbingsThe former OpenTable CEO and a16z investor explains supply, demand, unit economics and marketplace timing through lessons from OpenTable, Airbnb, eBay and Instacart.
53:50ENHenry Schuck on ZoomInfo, Sales Slowdowns and the Discipline of GrowthGast: Henry Schuck · Moderation: Harry StebbingsZoomInfo’s founder discusses bootstrapping, leadership, gratitude and how customer buying changed in the software market of early 2023.
1:08:53ENMaggie Hott on Building Enterprise Sales and Hiring the First RepsGast: Maggie Hott · Moderation: Harry StebbingsThe Webflow sales leader explains how to combine self-serve adoption with sales, build outbound and evaluate candidates.
1:05:07ENMartin Casado on Building Markets and Rethinking Venture CapitalGast: Martin Casado · Moderation: Harry StebbingsThe a16z general partner explains how an engineer became an investor, why founders need patient category-building, and how venture firms might scale.
1:16:12ENJason Lemkin on Finding SaaS Investments, Founder Feedback and the Algolia BetGast: Jason Lemkin · Moderation: Harry StebbingsThe SaaStr founder revisits an early investment in Algolia and explains how operator experience, honest competitive analysis and difficult conversations shape his venture practice.
58:09ENVaibhav Sahgal on Connecting Users to Value and Building Growth TeamsGast: Vaibhav Sahgal · Moderation: Harry StebbingsThe Reddit product leader shares lessons from Zynga on user research, protecting channels, hiring growth leaders and validating ideas before engineering them.
50:41ENLauren Schwartz on Hiring Salespeople and Building an Enterprise Sales TeamGast: Lauren Schwartz · Moderation: Harry StebbingsThe Fivetran enterprise sales leader discusses customer discovery, early hires, onboarding, deal reviews and aligning incentives with customer outcomes.
48:43ENEleanor Dorfman on Building Sales Teams, Playbooks and Customer-Centered ReviewsGast: Eleanor Dorfman · Moderation: Harry StebbingsThe Retool sales leader explains how founders can learn from early customers, hire for ambiguity and build repeatable sales practices.
1:03:46ENJordan Van Horn on Sales Playbooks, Hiring and Learning from DealsGast: Jordan Van Horn · Moderation: Harry StebbingsThe Monte Carlo revenue leader explains what founders should document, how to evaluate sales candidates and how to support a growing team.
1:06:16ENQuick-Commerce Economics: Airlift, JOKR and Zepto Founders Debate Emerging MarketsGast: Usman Gul, Ralf Wenzel, Aadit Palicha · Moderation: Harry StebbingsIn a 2022 roundtable, three founders compare fulfillment costs, basket size, fees and advertising while disagreeing about the economics of delivery speed.
54:17ENOliver Jay on Sales Playbooks, Hiring and Customer LearningGast: Oliver Jay · Moderation: Harry StebbingsThe former Dropbox and Asana sales leader explains why early teams should learn before treating a sales process as fixed and scalable.
2:16:07ENAsk What Could Go Right: Jason Calacanis on Robinhood, Loyalty, and Two Checks for TeslaGast: Jason Calacanis · Moderation: Lex FridmanThe angel investor and All-In co-host walks Lex Fridman from a Palo Alto dive bar to GameStop, Silicon Valley’s war on friction, and a friendship that kept a car company alive for twelve extra days.
1:26:27ENKai-Fu Lee: Originality Pride Is a Handcuff on What a Company Can BecomeGast: Kai-Fu Lee · Moderation: Lex FridmanIn a 2019 conversation with Lex Fridman, the investor and former Google China president explains why China's copycat years were a training ground, why data often beats clever algorithms, and what facing death did to his idea of work.
1:42:04ENPaid Growth, Step by Step: Shopify's Performance Marketing Lead on Tests, Signal and Team DesignGast: Timothy Davis · Moderation: 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.
1:15:29ENThe Zero-Day Marketing Exploits Behind Breakout StartupsModeration: Lenny RachitskyAlistair Croll explains how founders can find unfair distribution advantages by subverting platforms, norms, and regulations—without actually being evil.
1:21:35ENLook Outside the Building: Shaun Clowes on Why Most PMs Fall Short and How AI Changes the JobGast: Shaun Clowes · Moderation: Lenny RachitskyConfluent's chief product officer explains how to become a far better product manager, why data matters more than models, and what AI will and won't do to SaaS.
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