Sam Altman — portfolio autopsies

Collaborative online divorce for couples who wanted to split without litigation

The iBuying startup that held $10B in homes when mortgage rates doubled

Fashion rental subscription acquired Lord and Taylor department stores and collapsed in the pandemic

iBuyer pioneer that went public at $18B via SPAC and saw its stock fall 97% as rate hikes destroyed the model.

The Airbnb for science experiments ran out of runway before labs ran out of needs.

Creator economy platform hit $4B valuation — then laid off twice, cut valuation by half, and watched Substack steal the newsletter writers

The product analytics startup valued at $900M in 2021 — acquired by Contentsquare for ~$200M in 2023 as Amplitude and PostHog ate the market from both ends

The $176M AGI startup backed by Elon Musk and Jeff Bezos — acquired by Amazon for the engineers, not the AI.

iBuying pioneer. Fed rate rises doubled mortgage rates. Opendoor lost $1B in a quarter.

Free lab management for 150,000 scientists couldn't survive a corporate acquirer's monetization demands.

A beloved construction blueprint app sold for $875M then quietly dismantled by Autodesk.

A/B testing pioneer sold for a fraction of its valuation after free tools ate the market

Justin Kan's errand app sold for $10M then killed—proof that on-demand everything doesn't pencil out.

Justin Kan's Y Combinator errand startup — outpaced by TaskRabbit before reaching critical mass.