SV Angel — portfolio autopsies

Hollywood's prestige beauty curator couldn't build a sustainable D2C moat against Sephora and Goop

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.

Mortgage and banking technology SaaS company that went public at a 4.3 billion dollar valuation and watched revenues collapse 80 percent when US mortgage origination plummeted.

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

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

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

Legal marketplace for startups raised $11M and could not crack attorney buyer behavior

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

The Amazon brand aggregator raised $225M from General Atlantic to buy and scale FBA brands and quietly wound down when the aggregator model revealed structural unit-economic failures.

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

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

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

Israeli AI video creation startup raised $30M and was outcompeted by Canva and TikTok built-in tools

Andreessen Horowitz-backed premium remote work vacation rental startup raised $20M and shut down when it could not turn beautiful cabins into a profitable business.

The BI unicorn that spent $800M to build a category already owned by Tableau and Salesforce.

From $7B direct listing darling to 90% market cap wipeout

The Airbnb for science experiments ran out of runway before labs ran out of needs.

FarmVille creator — $10B IPO, Facebook algorithm change destroyed it overnight

GPT-4's legal breakthrough sold itself to the Westlaw empire for $650 million.

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

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

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

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

IPO at $7B, acquired by Naver for $1.2B — social commerce's 80% markdown in two years

Digital media's biggest SPAC at $1.5B. BuzzFeed News shut 18 months later. Stock down 95%.

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

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

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

Australia's DTC mattress and furniture brand. Post-COVID furniture demand collapsed.

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

Daily deals pioneer rejected Google's $6B offer. Stock fell 97%. CEO fired via shareholder letter. From 12,000 employees to under 500.

DTC mattress unicorn IPO'd at $575M in 2020 after raising $339M—then was taken private in 2022 at $6.90/share, down 79% from its IPO price, after years of losses proved the model unworkable.

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

Twitter paid $86M for live video in 2015 — then deleted 6 years of broadcasts to save server costs

Twitter's first creator bet, quietly killed six years after the $30M acquisition.

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

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

Even $70M and elite backers couldn't let location data compete with Google's monopoly.

The FTC blocked Harry's $1.37B acquisition by Edgewell — forcing the brand to compete alone at a scale it wasn't built for

SMB lending unicorn sold to AmEx for far below its $1.2B valuation — then the brand was quietly killed

The EHR startup valued at $1.5B, sold for $100M, then fined $145M for helping Purdue Pharma promote opioids

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

Sidewalk robot startup absorbed by Nuro before reaching commercial scale.

Built a $99 dedicated email device at the exact moment iPhone and Android launched — the smartphone revolution eliminated the need for dedicated email hardware within 2 years

Built a prettier job board for hourly workers and forgot to build a business model.

Shopping inside Instagram. Instagram built it themselves.

The YouTube creator empire that couldn't survive its pivot to streaming

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

The photo host that broke millions of websites overnight by ransoming its own users

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

Trained retail workers for interviews but couldn't train its own unit economics.

Dalton Caldwell's $50/year ad-free Twitter alternative — crowdfunded $750K in 30 days from developers, built a beloved product, and shut down because users wouldn't pay for social networking

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

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

The fastest-growing HR software startup in history — until it was exposed for letting employees sell insurance without licenses, triggering a $4.5B valuation collapse.

The always-on social app that killed your battery before it could build your network.

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

The most beautiful visual storytelling app that no one could figure out how to monetise

Banking APIs before the world was ready

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

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

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

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

The photo backup startup that lost its users' irreplaceable memories on the way down

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

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

Pioneered in-store mobile rewards, only to discover walking in isn't the same as buying.

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

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

Supreme Court killed the antenna startup the broadcast networks feared

Branch was invite-only public conversations between thought leaders. Facebook acquired it. Shut it down within months.

DailyBooth was an early web photo-sharing service that allowed users to share daily photos.

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

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

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

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

YC co-founder of today's YC President built "post by email" blogging. Twitter acquired it to improve posting UX. Shut it 13 months later.

The FarmVille empire — built on Facebook, destroyed when Facebook changed its newsfeed algorithm.

Insight into employees, exit from independence.

A social network for good causes that couldn't find its own cause.

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.

Long-distance ridesharing ran out of road before reaching scale

Chomp was an app search engine that allowed users to search for applications across multiple platforms including iOS and Android.

Canada's smart parcel locker startup — acquired by Google, then quietly killed.

An anonymous Q&A network that couldn't escape the shadow of Facebook and bullying

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

Local data API that couldn't find its market

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

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

White-label fan communities that couldn't build a community of their own success.

Pioneered social Q&A with AI routing — Google bought it for $50M and killed it in 14 months.

The content farm that sold before the algorithm killed the harvest

The power user's Twitter client, sacrificed on the altar of monetization

A content delivery SaaS that never found its signal in the noise

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

eBay's local experiment that couldn't survive the parent's pivot.

Shawn Fanning's gamer social network: acquired by EA, deleted by EA.