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1:15:51EN
20VC with Harry Stebbings· Oct 8, 2026Podcast · 4 speakersThe AI Race, Founder Loyalty and the New Rules of Enterprise SoftwareGuest Dev Ittycheria, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsHarry Stebbings, Dev Ittycheria, Jason Lemkin and Rory O’Driscoll debate model competition, startup exits and what happens when AI agents choose vendors.
1:16:00EN20VC with Harry Stebbings· Sep 7, 2026Podcast · 2 speakersJD Grèze on Building Town and Competing in AI AssistantsGuest Jean-Denis Greze · Host Harry StebbingsTown’s co-founder discusses privacy, model costs, competition and why he prioritizes customer value over token consumption.
1:32:50EN20VC with Harry Stebbings· Sep 18, 2025Podcast · 4 speakersKaz Nejatian on Opendoor, AI Financing and the Cost of GrowthGuest Kaz Nejatian, Jason Lemkin, Rory O’Driscoll · Host Harry StebbingsOpendoor’s new CEO explains his housing strategy; Harry Stebbings and investors examine AI infrastructure commitments, software margins and the return of IPOs.
1:10:18EN20VC with Harry Stebbings· May 13, 2024Podcast · 2 speakersTom Blomfield on YC, Fundraising and the Founder’s JobGuest Tom Blomfield · Host Harry StebbingsThe Monzo co-founder and YC partner discusses selecting founders, running a batch and balancing a large vision with immediate execution.
48:02EN20VC with Harry Stebbings· Mar 8, 2024Podcast · 2 speakersBrendon Cassidy on Early Sales Hiring, Discovery and OutboundGuest Brendon Cassidy · Host Harry StebbingsThe sales leader explains how he evaluates first hires, builds a customer-centered playbook and reviews deals, while questioning conventional outbound tactics.
1:38:44EN20VC with Harry Stebbings· Feb 5, 2024Podcast · 3 speakersDavid Tisch and Terrence Rohan on Seed Investing, Conviction and Founder RelationshipsGuest David Tisch, Terrence Rohan · Host Harry StebbingsTwo seed investors discuss price, group decisions, follow-on capital and the limits of investor influence—and disagree on signaling.
1:14:40EN20VC with Harry Stebbings· Jan 10, 2024Podcast · 3 speakersEd Sim and Jamin Ball on Startup Exits, IPOs and the 2024 Funding ResetGuest Ed Sim, Jamin Ball · Host Harry StebbingsTwo investors discuss the consequences of high private valuations, founder and investor incentives, acquisition markets and the path to an IPO.
41:30EN20VC with Harry Stebbings· Nov 17, 2023Podcast · 4 speakersRebecca Kaden, Nicole Quinn and Eurie Kim Debate Venture Pricing and AIGuest Rebecca Kaden, Nicole Quinn, Eurie Kim · Host Harry StebbingsThe investors discuss seed competition, a tighter Series B market, AI opportunities and how to finance companies after high valuations.
50:31EN20VC with Harry Stebbings· Oct 27, 2023Podcast · 2 speakersEd Sim on Seed Valuations, Inception Investing and Reserving for GrowthGuest Ed Sim · Host Harry StebbingsThe Boldstart founder explains his early financing framework, the risks of excess capital and why follow-on discipline matters.
1:01:06EN20VC with Harry Stebbings· Oct 25, 2023Podcast · 2 speakersEly Lerner on Startup Advisors, Growth Strategy and FocusGuest Ely Lerner · Host 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.
53:34EN20VC with Harry Stebbings· Oct 23, 2023Podcast · 2 speakersMatthieu Rouif on PhotoRoom's Focus, Mobile Growth and AI DesignGuest Matthieu Rouif · Host Harry StebbingsThe PhotoRoom co-founder explains how user testing, a narrow audience and mobile distribution shaped the photo-editing business.
46:15EN20VC with Harry Stebbings· Oct 12, 2023Podcast · 3 speakersMichael Eisenberg and Adi Levanon on Israel’s Tech Community After the October 2023 AttackGuest Michael Eisenberg, Adi Levanon · Host Harry StebbingsIn an interview published days after the Hamas-led attack, two investors describe family mobilisation, community support and disruption to startups.
1:24:10EN20VC with Harry Stebbings· Sep 20, 2023Podcast · 4 speakersIs the Venture Capital Model Broken? A Debate on Prices, Product-Market Fit and ReturnsGuest Eric Paley, Mike Maples, Jason Lemkin · Host Harry StebbingsEric Paley, Mike Maples and Jason Lemkin debate seed valuations, AI hype, fund returns and the choices founders face after raising too much.
1:10:33EN20VC with Harry Stebbings· Feb 27, 2023Podcast · 2 speakersDavid Tisch on Seed Fund Math, Valuations and Founder–Investor AlignmentGuest David Tisch · Host Harry StebbingsThe BoxGroup investor debates small checks, reserves and fundraising trade-offs with Harry Stebbings, and explains why he favors a flexible seed strategy.