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20VC with Harry Stebbings· Aug 8, 2026Podcast · 2 speakersDavid Frankel on Seed Investing, AI Winners and the Value of PatienceGuest David Frankel · Host Harry StebbingsFounder Collective’s co-founder debates fund size, valuations and exits with Harry Stebbings, and explains why he expects both transformative AI companies and heavy losses.
1:04:36EN20VC with Harry Stebbings· Jul 13, 2026Podcast · 2 speakersWix CEO Avishai Abrahami on Base44, AI and Building for Small BusinessesGuest Avishai Abrahami · Host Harry StebbingsThe Wix co-founder discusses AI-assisted application building, software economics, customer support and leadership through market uncertainty.
1:04:15EN20VC with Harry Stebbings· Mar 7, 2026Podcast · 2 speakersMitchell Green on Software Stocks, Venture Liquidity and Investing Through AI ChangeGuest Mitchell Green · Host Harry StebbingsThe Lead Edge founder explains his approach to buying, selling and assessing retention while debating AI disruption and venture-fund economics.
1:14:16EN20VC with Harry Stebbings· Mar 2, 2026Podcast · 2 speakersEran Zinman on Monday.com’s AI Pivot, Pricing and Software MarketsGuest Eran Zinman · Host Harry StebbingsThe Monday.com CEO discusses AI-built software, agent workflows, sales automation and leading a public company through a difficult market.
1:06:37EN20VC with Harry Stebbings· Feb 23, 2026Podcast · 2 speakersLucas Swisher on AI Growth Investing, Fund Size and the Price of ScaleGuest Lucas Swisher · Host Harry StebbingsThe Coatue growth investor discusses software valuations, concentrated funds, AI economics and the judgment behind follow-on investments.
1:29:46EN20VC with Harry Stebbings· Feb 16, 2026Podcast · 2 speakersKlarna CEO Sebastian Siemiatkowski on AI, Software and the Future of BankingGuest Sebastian Siemiatkowski · Host Harry StebbingsThe Klarna cofounder explains his predictions about software switching costs, customer service and a digital financial assistant, while discussing the pressures of building a public company.
1:20:02EN20VC with Harry Stebbings· Feb 9, 2026Podcast · 2 speakersAnish Acharya on AI Software, Investment Judgment and the Limits of AutomationGuest Anish Acharya · Host Harry StebbingsThe a16z investor discusses incumbent software, agent products, pricing, margins and the choices founders face in a fast-moving market.
1:18:29EN20VC with Harry Stebbings· Nov 24, 2025Podcast · 2 speakersBase44 Founder Maor Shlomo on AI App Building and CompetitionGuest Maor Shlomo · Host Harry StebbingsShlomo explains why he joined Wix, how he thinks about app-builder defensibility and why the future of software remains contested.
1:23:11EN20VC with Harry Stebbings· Aug 25, 2025Podcast · 2 speakersBessemer’s Byron Deeter on AI Growth, Venture Scale and LiquidityGuest Byron Deeter · Host Harry StebbingsDeeter discusses AI software economics, follow-on investments and the trade-offs facing venture firms and their limited partners.
1:07:38EN20VC with Harry Stebbings· Aug 21, 2024Podcast · 2 speakersAman Narang on Building Toast: Speed, Focus and Scaling a Restaurant PlatformGuest Aman Narang · Host Harry StebbingsThe Toast co-founder explains how the company pivoted to point of sale, learned to scale its team and expanded into payments and lending.
1:05:48EN20VC with Harry Stebbings· Aug 14, 2024Podcast · 2 speakersKaz Nejatian on Shopify: Building Complete Products and a Company for the Long TermGuest Kaz Nejatian · Host Harry StebbingsShopify’s COO explains its product culture, internal tools and partnerships, and reflects on remote work, information flow and leadership.
50:08EN20VC with Harry Stebbings· Aug 9, 2024Podcast · 2 speakersDax Dasilva on Bootstrapping Lightspeed, Growth and Returning as CEOGuest Dax Dasilva · Host Harry StebbingsThe Lightspeed founder explains how close customer observation shaped its product, why he returned to lead a profitable-growth transition, and what acquisitions left unfinished.
1:07:40EN20VC with Harry Stebbings· Jul 15, 2024Podcast · 2 speakersSaam Motamedi on AI Valuations, Series B Risk and Backing FoundersGuest Saam Motamedi · Host Harry StebbingsThe Greylock partner explains why he sees exuberant AI pricing, questions a universal Series A revenue threshold, and favors founder and market judgment over simple checklists.
45:11EN20VC with Harry Stebbings· Jul 12, 2024Podcast · 2 speakersMark Roberge on Sales Hiring, Unit Economics and Moving UpmarketGuest Mark Roberge · Host Harry StebbingsThe former HubSpot sales leader explains how founders can build a sales motion, align incentives and decide when enterprise customers are worth pursuing.
1:20:50EN20VC with Harry Stebbings· Jun 3, 2024Podcast · 2 speakersJason Lemkin on SaaS Valuations, Private Equity and the Liquidity ProblemGuest Jason Lemkin · Host Harry StebbingsThe SaaStr founder discusses slowing software growth, AI budgets, venture returns and why the next exit may be harder to find.
1:24:54EN20VC with Harry Stebbings· May 27, 2024Podcast · 2 speakersJason Lemkin on SaaS Investing, Churn and Seed ValuationsGuest Jason Lemkin · Host Harry StebbingsThe SaaStr founder revisits successful and disappointing deals, explains his diligence process and assesses the economics of seed investing.
59:47EN20VC with Harry Stebbings· May 22, 2024Podcast · 2 speakersAaron Levie on AI Agents, SaaS Pricing and the Race Between Startups and IncumbentsGuest Aaron Levie · Host Harry StebbingsThe Box CEO considers how AI might change business workflows, employment and software pricing, and why established companies and startups both have a chance.
52:52EN20VC with Harry Stebbings· Apr 19, 2024Podcast · 2 speakersGirish Mathrubootham on Freshworks Pricing, Products and ScalingGuest Girish Mathrubootham · Host Harry StebbingsThe Freshworks founder shares lessons from self-service software, a multi-product strategy, executive hiring and investing in Indian startups.
1:12:20EN20VC with Harry Stebbings· Jan 31, 2024Podcast · 2 speakersDave Kellogg on SaaS Metrics, Sales Forecasting and Efficient GrowthGuest Dave Kellogg · Host Harry StebbingsThe software executive explains why he separates acquisition, retention and margin, and offers practical ways to improve forecasting and customer relationships.
1:32:52EN20VC with Harry Stebbings· Jan 4, 2024Podcast · 2 speakersJason Lemkin on SaaS, Venture and His 2024 PredictionsGuest Jason Lemkin · Host Harry StebbingsThe SaaStr founder reviews a difficult 2023, reconsiders exit advice and debates what could change for startups in 2024.
55:24EN20VC with Harry Stebbings· Dec 13, 2023Podcast · 2 speakersSteve Goldberg on Selling to CFOs, Reviewing Deals and Building Customer TrustGuest Steve Goldberg · Host Harry StebbingsThe Salesloft revenue leader explains how to find a real champion, demonstrate business outcomes and make renewals part of the sales process.
1:25:06EN20VC with Harry Stebbings· Dec 4, 2023Podcast · 2 speakersTooey Courtemanche on Procore's Long Road to Growth and the Work of LeadingGuest Tooey Courtemanche · Host Harry StebbingsThe construction software founder discusses surviving a slow market, building a product platform, delegating and balancing a company with family life.
57:34EN20VC with Harry Stebbings· Nov 10, 2023Podcast · 2 speakersChris Degnan on Building Snowflake's Sales Team from the First CustomerGuest Chris Degnan · Host Harry StebbingsSnowflake's revenue chief explains prospecting, customer feedback, forecasting and his unconventional view of customer success.
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.Load moreShowing 24 of 29