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58:26ENGili Raanan on Venture Entry Prices, Growth and Private-Market LiquidityGuest Gili Raanan · Host Harry StebbingsThe Cyberstarts founder explains his approach to cybersecurity investing, when he discusses margins and why secondary sales can help employees and limited partners.
1:15:28ENMike Maples on Seed Investing, Founder Fit and When to SellGuest Mike Maples · Host Harry StebbingsThe Floodgate investor explains his approach to fund economics, exceptional founders, follow-ons and partial exits.
50:08ENDax 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.
1:10:18ENTom 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.
1:02:14ENRujul Zaparde on Building Zip, Hiring for Potential and Moving FastGuest Rujul Zaparde · Host Harry StebbingsThe Zip co-founder explains how a procurement problem became a company, why repeatability matters, and how he balances speed with creativity and careful hiring.
1:44:48ENDaniel Dines on Building UiPath, Risk and Finding PeaceGuest Daniel Dines · Host Harry StebbingsThe UiPath founder traces his path from learning C++ without a computer to finding a global market for automation, and reflects on leadership, money and the costs of growth.
52:54ENVickie Peng on Building Less, Measuring Customer Value and Finding Product-Market FitGuest Vickie Peng · Host Harry StebbingsThe Sequoia product leader explains how to learn with less product, choose meaningful metrics and recognize different customer mindsets.
1:09:17ENGili Raanan on Seed Investing, Founder Selection and Cyberstarts’ Sunrise ProcessGuest Gili Raanan · Host Harry StebbingsThe Cyberstarts founder explains his focus on teams, structured customer discovery and building cybersecurity companies.
1:24:10ENIs 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.
1:10:10ENBrian Balfour on Growth Loops, Channel Fit and Building a Repeatable Growth SystemGuest Brian Balfour · Host Harry StebbingsThe Reforge founder and former HubSpot growth leader explains how to identify constraints, choose channels and avoid mistaking attention for sustainable growth.
1:18:41ENGuy Podjarny on Snyk, Product-Market Fit and Building Durable AdvantageGuest Guy Podjarny · Host Harry StebbingsThe Snyk founder and angel investor explains how to reason about future markets, focus messaging and learn through iteration.
1:33:36ENMike Salguero on Bootstrapping ButcherBox and Subscription EconomicsGuest Mike Salguero · Host Harry StebbingsThe ButcherBox founder explains customer acquisition, per-box margins and the trade-offs behind building without venture capital.
1:03:08ENJag Duggal on Customer Discovery, Product Strategy and Scaling NubankGuest Jag Duggal · Host Harry StebbingsNubank’s product leader explains why clear hypotheses, customer love and small autonomous teams matter as a company grows.
1:03:41ENAdam Grenier on Building Growth into the BusinessGuest Adam Grenier · Host Harry StebbingsThe former Uber growth leader explains marketplace acquisition, hiring, retention and the limits of attribution through lessons from Uber, Lambda School and MasterClass.
1:01:55ENMike Duboe on Growth Teams, Experiments and Paid MarketingGuest Mike Duboe · Host Harry StebbingsThe former Stitch Fix growth leader explains how to choose meaningful metrics, hire for growth and test whether marketing actually creates demand.









