E33: Y Combinator, Open Source, and Lifting Founders Up with Jason Freedman

Jason Freedman is a serial founder and General Partner at Orange Collective. Orange Collective is a Y Combinator-focused venture fund that aims to invest in the most promising YC companies before Demo Day. We talked about YC, exits, AI, open source, raising founders up, and why ownership percentages are overrated. We also discussed:   YC’s radical candor + optimism Orange Collective’s super-power: “use the product” diligence Early, relationship-first checks beat ownership math Real-world example: Mastra AI Doubling down on AI infrastructure Why open-source wins long-term Exits require as much craft as fundraising “Raise founders up” in practice Ownership percentages are overrated   Investing in Startups is hosted by Joe Magyer and produced by Seaplane Ventures.