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1:15:51ENThe AI Race, Founder Loyalty and the New Rules of Enterprise SoftwareGast: Dev Ittycheria, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsHarry Stebbings, Dev Ittycheria, Jason Lemkin and Rory O’Driscoll debate model competition, startup exits and what happens when AI agents choose vendors.
1:16:00ENJD Grèze on Building Town and Competing in AI AssistantsGast: Jean-Denis Greze · Moderation: Harry StebbingsTown’s co-founder discusses privacy, model costs, competition and why he prioritizes customer value over token consumption.
1:32:50ENKaz Nejatian on Opendoor, AI Financing and the Cost of GrowthGast: Kaz Nejatian, Jason Lemkin, Rory O’Driscoll · Moderation: Harry StebbingsOpendoor’s new CEO explains his housing strategy; Harry Stebbings and investors examine AI infrastructure commitments, software margins and the return of IPOs.
1:10:18ENTom Blomfield on YC, Fundraising and the Founder’s JobGast: Tom Blomfield · Moderation: Harry StebbingsThe Monzo co-founder and YC partner discusses selecting founders, running a batch and balancing a large vision with immediate execution.
48:02ENBrendon Cassidy on Early Sales Hiring, Discovery and OutboundGast: Brendon Cassidy · Moderation: Harry StebbingsThe sales leader explains how he evaluates first hires, builds a customer-centered playbook and reviews deals, while questioning conventional outbound tactics.
1:38:44ENDavid Tisch and Terrence Rohan on Seed Investing, Conviction and Founder RelationshipsGast: David Tisch, Terrence Rohan · Moderation: Harry StebbingsTwo seed investors discuss price, group decisions, follow-on capital and the limits of investor influence—and disagree on signaling.
1:14:40ENEd Sim and Jamin Ball on Startup Exits, IPOs and the 2024 Funding ResetGast: Ed Sim, Jamin Ball · Moderation: Harry StebbingsTwo investors discuss the consequences of high private valuations, founder and investor incentives, acquisition markets and the path to an IPO.
41:30ENRebecca Kaden, Nicole Quinn and Eurie Kim Debate Venture Pricing and AIGast: Rebecca Kaden, Nicole Quinn, Eurie Kim · Moderation: Harry StebbingsThe investors discuss seed competition, a tighter Series B market, AI opportunities and how to finance companies after high valuations.
50:31ENEd Sim on Seed Valuations, Inception Investing and Reserving for GrowthGast: Ed Sim · Moderation: Harry StebbingsThe Boldstart founder explains his early financing framework, the risks of excess capital and why follow-on discipline matters.
1:01:06ENEly Lerner on Startup Advisors, Growth Strategy and FocusGast: Ely Lerner · Moderation: Harry StebbingsThe former Yelp and Chime product leader explains how to choose and compensate advisors, identify a growth lever, and balance strategic bets with essential defensive work.
53:34ENMatthieu Rouif on PhotoRoom's Focus, Mobile Growth and AI DesignGast: Matthieu Rouif · Moderation: Harry StebbingsThe PhotoRoom co-founder explains how user testing, a narrow audience and mobile distribution shaped the photo-editing business.
46:15ENMichael Eisenberg and Adi Levanon on Israel’s Tech Community After the October 2023 AttackGast: Michael Eisenberg, Adi Levanon · Moderation: Harry StebbingsIn an interview published days after the Hamas-led attack, two investors describe family mobilisation, community support and disruption to startups.
1:24:10ENIs the Venture Capital Model Broken? A Debate on Prices, Product-Market Fit and ReturnsGast: Eric Paley, Mike Maples, Jason Lemkin · Moderation: Harry StebbingsEric Paley, Mike Maples and Jason Lemkin debate seed valuations, AI hype, fund returns and the choices founders face after raising too much.
1:10:33ENDavid Tisch on Seed Fund Math, Valuations and Founder–Investor AlignmentGast: David Tisch · Moderation: Harry StebbingsThe BoxGroup investor debates small checks, reserves and fundraising trade-offs with Harry Stebbings, and explains why he favors a flexible seed strategy.
1:01:56ENMike Cessario on Building Liquid Death as a Beverage and Entertainment BrandGast: Mike Cessario · Moderation: Harry StebbingsThe Liquid Death founder explains the thinking behind its irreverent marketing, the difficulty of beverage distribution and why he prizes creative ideas that people share.
1:00:19ENWilliam Hockey on Plaid, Column and Building Financial InfrastructureGast: William Hockey · Moderation: Harry StebbingsThe Plaid co-founder explains why he started a regulated bank, how he thinks about patient hiring and what he expects from the next decade of fintech.
1:08:42ENParker Conrad on Rippling, Connected Products and Starting AgainGast: Parker Conrad · Moderation: Harry StebbingsThe Rippling founder discusses his compound-startup strategy, shared employee data, cross-selling and the lessons he draws from earlier ventures.









