First Round — 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

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

Pioneering US digital bank acquired by BBVA for 117 million dollars in 2014 and quietly killed seven years later when the acquirer decided it no longer fit the strategy.

The millennial Costco raised $500M and filed bankruptcy the same year it went public

35 million recipe lovers lost all their saved meals when Whirlpool pulled the plug.

DTC eyewear pioneer that went public at $6B — then discovered retail stores cost as much as the old retail model

The largest fleet of Earth imaging satellites — SPAC'd at $2.8B, now a penny stock struggling for survival

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

Argentina's BCRA regulations and a parent company pivot ended Simple before it could prove its model.

Pay-per-mile car insurance for people who barely drive. The drivers who signed up barely drove — and barely paid.

The original neo-bank — killed not by the market but by the acquirer.

Laid off everyone in 2019, rebuilt alone, then couldn't raise the $20M it needed to win.

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

The adaptive learning giant that raised $105M promising AI-powered personalisation and sold for $25M

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

The original content discovery app — killed by eBay's acquisition and then its own founders' buyback

A $118M drone empire that collapsed overnight with zero severance.

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

The flash sale home décor unicorn that Bed Bath & Beyond bought for less than its last funding round

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

The design flash-sale unicorn that raised $336M, grew to 2,000 employees in 18 months — and sold the whole thing for $15M

Design flash-sale site pivoted four times and ran out of identity

Home cleaning marketplace killed by worker misclassification lawsuits

The $38M home cleaning marketplace killed by worker misclassification lawsuits before it could scale

Turned digital photos into real postcards — but couldn't turn novelty into loyalty.

Supreme Court killed the antenna startup the broadcast networks feared

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

The inbox intelligence startup that turned down Microsoft and sold to Yahoo

The virtual DJ room that built the internet's most social music experience — and was shut down by music licensing costs

Built the social layer for barcodes, then discovered nobody was going to scan anything.

Revenue analytics that couldn't generate its own revenue.

Campus recruiting's bright promise, ended by an acqui-hire

Betting $43M that people love ads enough to save them.

Matching skills to needs — but the marketplace never reached critical mass.

The social media management pioneer swallowed by the enterprise cloud machine.

Optimizing paid search until the big players made it their feature

The music social network with 23M users that let you stream any song for free — destroyed by record label licensing terms that charged $0.25 per stream before Spotify existed

Browser speed-up killed by the browsers it tried to fix