Alexis Ohanian — portfolio autopsies

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

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

Hipmunk built a better flight search and was acquired by Concur — then SAP decided a beloved flight search app was not part of its enterprise travel platform strategy

The product analytics startup valued at $900M in 2021 — acquired by Contentsquare for ~$200M in 2023 as Amplitude and PostHog ate the market from both ends

The note-taking unicorn that tried to become a platform — and got outclassed by apps that just took better notes.

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

Creator economy platform hit $4B valuation — then laid off twice, cut valuation by half, and watched Substack steal the newsletter writers

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

Mexico's electric scooter unicorn hopeful. It ran out of money before running out of sidewalks.

$364M couldn't make exploitative lending ethical — regulators noticed.

A beloved construction blueprint app sold for $875M then quietly dismantled by Autodesk.

Parking app swallowed by its own merger after Google entered the space.

Influencer-curated quarterly boxes couldn't generate enough recurring revenue to survive.

Ten-dollar restaurant food in 10 minutes required kitchen density that could never pencil out

Justin Kan's errand app sold for $10M then killed—proof that on-demand everything doesn't pencil out.

Frontback was a social app for sharing selfies from front and back cameras simultaneously.

The anonymous sharing app that hit #1 in the App Store — and shut down 15 months later because anonymity enables cruelty at scale

Justin Kan's Y Combinator errand startup — outpaced by TaskRabbit before reaching critical mass.

The YC-backed tutor marketplace that could not survive its own unit economics

16 million downloads via viral spam tricks, then a $60M exit before the music stopped.