Keith Rabois — portfolio autopsies

Legal research AI startup acquired by Fastcase before it could challenge LexisNexis and Westlaw at scale.

The Amazon brand aggregator raised $225M from General Atlantic to buy and scale FBA brands and quietly wound down when the aggregator model revealed structural unit-economic failures.

Discount marketplace IPO'd at $14B then sold for $173M three years later

Amazon for the price-sensitive: $1 items shipped free, no questions asked

The online course marketplace that couldn't turn 60,000 courses into profits

Pre-prepped dinner kits couldn't out-innovate the industry's systemic churn problem.

The radical transparency fashion brand that was opaque about its own culture — exposed during the racial justice moment of 2020

The enterprise social network that won the market, sold to Microsoft — and got integrated too slowly to survive Slack.

Dave Morin's "thoughtful" private social network raised $60M to fix Facebook. Sold to Kakao for a nominal sum. Shut down in 2018.

Check-in for TV shows sounded clever until nobody cared what their friends were watching.