Redpoint Ventures — portfolio autopsies

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

Hamburg Airbnb competitor raised 12 million euros, survived eight years in the shadow of Airbnb, and was absorbed by Wimdu right before both shut down.

Latin America's English-learning giant sold for cents on the dollar after burning $120M.

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

P2P car sharing with $300M from SoftBank. Insurance costs and maintenance ate every dollar. Filed Chapter 11 in December 2023.

The $17B customer service platform that tried to buy SurveyMonkey for $4.1B, got blocked by shareholders, and ended up going private at a $6.8B discount to its peak

China's original short-video king had 300M users — then Douyin arrived and erased it.

The crowdsourced same-day delivery network for retailers that shut down as COVID shifted e-commerce to Amazon-scale logistics.

Gaming YouTube MCN with 12B monthly views and 180M subscribers was acquired by AT&T/Otter Media. Shut January 2019. All 40,000+ YouTube channels and years of content deleted overnight.

The $1B Hadoop unicorn that the cloud giants made obsolete before it could go public

The mobile strategy gaming company that hit $400M in revenue at its peak — then watched the mobile gaming market consolidate around a handful of mega-titles

A single card that stored all your credit cards electronically — made obsolete by Apple Pay and Google Pay before it could achieve scale.

The peer-to-peer used car marketplace that burned $150 million and never solved operations

The "Tinder for jobs" app was acquired by Monster Worldwide in 2016 and shut down 11 months later when Monster itself was acquired by Randstad.

The $110M startup that tried to build an Android without Google — raised money from Qualcomm, Microsoft, and Samsung to unseat Google's control of mobile, and shut down after 3 years

Home cleaning marketplace killed by worker misclassification lawsuits

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

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

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.

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

$970M solar startup killed by cheap Chinese panels and a government loan scandal

Andy Rubin's pre-Android startup — built the iconic T-Mobile Sidekick, sold to Microsoft for $500M, and watched its work become the Microsoft Kin: a phone discontinued 48 days after launch

Built the first mobile video streaming network — went bankrupt because customers would not pay their bills.