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.