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1:05:56ENAaron Katz on ClickHouse, AI Revenue Durability and Enterprise DataGast: Aaron Katz · Moderation: Harry StebbingsClickHouse’s CEO discusses agent workloads, open models, fundraising and the metrics he uses to judge durable growth.
1:04:33ENPhilipp Freise on KKR’s European Investing and Private-Market LiquidityGast: Philipp Freise · Moderation: Harry StebbingsThe KKR investor discusses deployment discipline, AI, European capital markets and broader access to private investments.
1:19:32ENBenchmark, a16z and the Math of Venture Capital in the AI EraGast: Rory O’Driscoll, Jason Lemkin · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate stage focus, large funds and how AI could reshape software and employment.
1:35:02ENa16z, Founders Fund and the Risks Behind Venture’s Biggest FundsGast: Rory O’Driscoll, Jason Lemkin · Moderation: Harry StebbingsHarry Stebbings, Rory O’Driscoll and Jason Lemkin debate fund size, late-stage returns, AI uncertainty and delayed liquidity.
1:10:19ENCarvana CEO Ernie Garcia on Conviction, Debt and Building Through Difficult MarketsGast: Ernest Garcia · Moderation: Harry StebbingsThe co-founder reflects on fundraising, operations, public markets and the personal trade-offs of leading a company.
1:24:12ENMitchell Green on Finding Software Companies and Returning Capital to InvestorsGast: Mitchell Green · Moderation: Harry StebbingsLead Edge Capital’s founder explains his sourcing framework, exit discipline and skepticism about paying high prices for AI.
1:12:05ENPeter Singlehurst on Growth Investing, Mistakes and Private-Market LiquidityGast: Peter Singlehurst · Moderation: Harry StebbingsBaillie Gifford’s head of private companies explains how he assesses durable business models, reinvestment decisions and investment risk.
1:12:13ENNiklas Östberg on Delivery Hero’s Growth, Acquisitions and the Cost of Moving Too FastGast: Niklas Östberg · Moderation: Harry StebbingsThe Delivery Hero founder reflects on pandemic-era financing, a costly Gorillas investment and how to distinguish sustainable delivery growth from subsidized volume.
1:33:55ENJake Saper on Zoom, AI and the Hard Decision of When to SellGast: Jake Saper · Moderation: Harry StebbingsThe Emergence Capital partner explains collective diligence, fund distributions and the trade-off between liquidity and holding winners.
1:09:19ENOscar Pierre on Glovo’s Fight for Funding, Expansion and Sale to Delivery HeroGast: Oscar Pierre · Moderation: Harry StebbingsThe Glovo founder recounts a pivotal McDonald’s deal, repeated financing crises, a costly Brazil expansion and the decision to join Delivery Hero.
57:31ENTS Anil on Monzo’s Turnaround, Product Strategy and Global AmbitionsGast: TS Anil · Moderation: Harry StebbingsThe Monzo CEO explains how the bank addressed interlocking funding and control problems, built a diversified revenue model and is thinking about expansion.
1:12:04ENCarlos Delatorre on Hiring Salespeople and Building a Repeatable PipelineGast: Carlos Delatorre · Moderation: Harry StebbingsThe Harness CRO explains why account executives should prospect, how he structures a weekly pipeline routine, and how sales leaders can train and evaluate their teams.
1:01:47ENEran Zinman on monday.com’s Pivot, Marketing Engine and Move UpmarketGast: Eran Zinman · Moderation: Harry StebbingsThe monday.com co-founder explains how early customer feedback, cash-focused marketing and a multi-product platform shaped the company’s growth.
1:10:55ENMatt Plank on Building Rippling’s Sales Organization and Scaling OutboundGast: Matt Plank · Moderation: Harry StebbingsThe Rippling CRO explains how his team plans capacity, works with marketing, prices deals and adapts its sales model as the product portfolio grows.
1:14:15ENZachary Bookman on OpenGov, Venture Capital and a $1.8 Billion SaleGast: Zachary Bookman · Moderation: Harry StebbingsThe OpenGov CEO discusses enterprise sales, founder–investor incentives, acquisitions and the long path to liquidity.
1:01:08ENGeorge Arison on Grindr’s Network, New Products and Lean Operating ModelGast: George Arison · Moderation: Harry StebbingsThe Grindr CEO discusses subscriptions, advertising, potential health and travel products, and the management choices behind a small team.
1:04:51ENCem Sertoglu on UiPath, Venture Risk and Backing FoundersGast: Cem Sertoglu · Moderation: Harry StebbingsThe investor recounts the decisions behind UiPath’s returns and explains how he thinks about founder relationships, reserves, valuation and liquidity.
58:31ENBen Fiechtner on Deal Design, Forecasting and Building Sales TeamsGast: Ben Fiechtner · Moderation: Harry StebbingsClari’s chief revenue officer explains his quarterly sales cadence, how to find real buying constraints, and what he looks for when hiring.
1:13:51ENSean Murray on Teaching Buyers and Moving into Enterprise SalesGast: Sean Murray · Moderation: Harry StebbingsThe Greenhouse revenue leader explains how he approaches discovery, renewals, enterprise readiness and sales hiring.
1:06:13ENShyam Sankar on Defense Procurement, Software and Building TalentGast: Shyam Sankar · Moderation: Harry StebbingsPalantir’s CTO argues for changing how governments buy technology and explains his approach to product, hiring and AI.
56:44ENHowie Liu on Airtable’s Enterprise Strategy and AI AdoptionGast: Howie Liu · Moderation: Harry StebbingsThe Airtable founder discusses product-led growth, enterprise buying, AI implementation and the work that follows product-market fit.
1:02:21ENNoah Weiss on Product-Led Growth and Scaling SlackGast: Noah Weiss · Moderation: Harry StebbingsSlack’s product leader discusses product principles, enterprise growth, speed and the lessons from products that did not work.









