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.

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