FLOODGATE — portfolio autopsies

Social product discovery for 11M users — Instagram Shopping and Pinterest Shopping provided native product tagging that eliminated the need for a separate social shopping app

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

India BNPL neobank backed by Tiger Global at $1.5B that merged with North East Small Finance Bank in 2023 after RBI rules eliminated its standalone fintech model.

The homework help unicorn IPO'd at $7B and lost 80% of its value the day ChatGPT made its core product obsolete

Loyalty SaaS for restaurants that couldn't retain loyalty from restaurants.

Non-invasive glucose monitor startup that couldn't solve the hard physics problem it was built on.

Native ad pioneer swallowed by SSP consolidation after 13 years of independence.

A social shopping feed of 30M products that could not convert browsing into buying

The original gig economy marketplace — saved by IKEA after a near-fatal pivot nearly destroyed it.

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

Shoppable photos before Pinterest Shopping — the right idea with no platform to live on

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

The $60M education tablet that tried to replace the college backpack and found the iPad had already won

Kevin Rose raised $45M for social news and declined a $200M Google offer. Digg v4 redesign in 2010 destroyed the community overnight. Users fled to Reddit. Sold for approximately $500K in 2012.

Gowalla built the better check-in app. Foursquare built the better network. Facebook acquired Gowalla for the team.

Kevin Rose built a better Twitter with file sharing. Two weeks after acquisition, it was gone.