Khosla Ventures — portfolio autopsies

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

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

Satellite imaging pioneer acquired by Google for $500M, sold to Planet Labs for $25M, and retired — a 95% write-down.

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

Neuroscience-based talent assessment raised 57 million dollars and was acquired by Harver but the product was wound down within a year as large language models commoditized its core differentiation.

The farm management software pioneer was absorbed into Corteva's ag-data empire

SMB invoice lender collapsed when credit markets tightened and charge-offs spiked.

Smart windows that tint automatically to save energy. Buildings didn't want to pay smart-window prices.

The payment platform that let businesses pay any invoice with a credit card — then filed for Chapter 11 as interest rate rises made the arbitrage impossible

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

Clinical graph AI trapped by HIPAA data walls while IBM and Google captured the market.

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

Raised $100M to compete with Amazon and Google in home security—and lost.

VC-backed BI darling couldn't escape Tableau's shadow despite $27M and A-list investors.

Real-time ad analytics pioneer quietly absorbed into Snap for a fraction of its promise.

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

The wearable pioneer that got crushed by the giants it inspired.

$3.2B for fitness trackers that broke. Apple Watch arrived.

Plant-based mayo unicorn — caught buying its own product off shelves

Vinod Khosla's cellulosic biofuel company that promised to convert wood chips into gasoline — Mississippi State invested $75M and sued for fraud when production never materialised

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

Taught the internet to make decisions — eBay bought it and buried it.

Meebo let you use AIM, MSN, and Yahoo Messenger in a browser tab. Google acquired it. Shut it down in 6 weeks.

Khosla Ventures' cellulosic ethanol company that received a $162M DOE loan — built a Georgia plant, never reached commercial scale, and was sold for parts when the loan defaulted