Tax Bill and Nonprofit Status: A Double-Edged Sword

What happens when Sam gets fed up with shady secondary brokers mid-recording?

He starts vibe coding a platform to replace them—live on the pod!

On this week’s More or Less, the gang dives deep into the messy mechanics of the secondary markets and how early cashouts might be a bigger red flag than anyone wants to admit.

Plus:

• Airbnb’s déjà vu product strategy
• The quiet crisis in venture liquidity (and who’s actually good at selling)
• OpenAI’s new “CEO of Applications”, and
• The looming threat of Trump’s nonprofit tax crackdown (and what it means for Harvard, endowments, and… Froyo)

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1) Sam Lessin: https://x.com/lessin

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