More or Less #99: The Airbnb Strategy Nobody’s Talking About
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May 16, 2025 The hosts tackle the frustrations of shady brokers in investment transactions, proposing a new service for transparency. They humorously discuss Airbnb’s evolving strategies, including intriguing partnerships with OnlyFans. A critical look at the secondary market in venture capital reveals the implications of early cash-outs for startups. The looming threat of a tax bill affecting nonprofit statuses adds a layer of complexity for institutions like Harvard. Plus, whimsical ideas for enhancing Airbnb experiences spark a fun conversation!
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Secondary Market Broker Frustration
- Sam Lessin shares frustration with secondary market brokers misrepresenting access and bids.
- He is coding a platform live to fix the broken, untrustworthy secondary market dynamics.
Selling Skills Lag Buying in Venture
- Selling in venture investing requires many more reps to master than buying.
- The broken secondary market partly arises because so few have experience selling early-stage stakes.
Founder Early Secondaries Signal Risks
- Early meaningful founder secondaries typically correlate with poor company outcomes.
- Small secondary cashouts for personal needs can be understandable, but large early sales are red flags.