Dave Morin — portfolio autopsies

Microsoft acquired Sunrise for $100M for its beautiful calendar design — then shut Sunrise 12 months later and launched Outlook Mobile with the same features

Enterprise content marketing platform that raised $74M and was acquired by Seismic below last round valuation.

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

Anonymous Q&A social had 30M users before cyberbullying cases linked to teen suicides made App Store restrictions and major media criticism inevitable

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

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

Pioneered the beauty subscription box at $485M. Sephora copied it. Sold for $1 to Walgreens in 2021.

$40B fintech. Restricted GameStop trading. Congressional hearings. Stock never recovered.

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

The office management startup that raised $89M to bring the gig economy to corporate facilities — then was acquired by WeWork for less than it raised, and wound down when WeWork imploded

Real-time friend radar was creepy enough that users deleted it within days.

The atomic news app that broke stories into digestible facts — shut down when social media made that a feature, not a business

28 million users loved asking anonymous questions. Some of those questions were horrifying.