Anti-Portfolio

Bessemer Venture Partners — Passed multiple times. David Cowan famously avoided meeting the founders when they were renting a garage from his college friend.

Source: Bessemer anti-portfolio page

Bessemer Venture Partners — Cowan's college friend said 'Here's a chance to invest in Apple.' Response: 'No thank you.'

Source: Bessemer anti-portfolio page

Bessemer Venture Partners — Stamp collecting? No. People exchanging pennies over the internet? 'No thank you.'

Source: Bessemer anti-portfolio page

Bessemer Venture Partners — Saw a $200M opportunity. Missed a trillion-dollar company.

Source: Bessemer anti-portfolio page

Bessemer Venture Partners — Why would anyone rent a stranger's spare bedroom?

Source: Bessemer anti-portfolio page

Bessemer Venture Partners — Passed on the seed round.

Source: Bessemer anti-portfolio page

Sequoia Capital — Asked to see a prototype before funding — company had sent a demo video. Passed after seeing the video.

Source: Dropbox founding story

Benchmark Capital — Mitch Lasky passed — thought disappearing photos was a niche feature, not a platform.

Source: Various interviews

Benchmark Capital — Peter Fenton passed on the seed round. Later became one of the best VC bets ever via Series A.

Source: Bloomberg profile

Various (multiple passes) — Many top VCs passed saying 'payments is a crowded space' before a16z and Sequoia invested.

Source: Stripe founding story

Sequoia Capital — Passed on Series A citing 'crowded video conferencing market' (Skype, WebEx, Hangouts).

Source: Sequoia interview

Multiple VCs — Another social news aggregator in an era of Digg? Most VCs passed.

Source: Reddit S-1 prospectus

Sequoia Capital — Jim Goetz was the exception — Sequoia invested. But many other top firms passed citing 'no monetization'.

Source: Various

Multiple VCs — Enterprise chat tool in a space dominated by email? Many passed on early rounds.

Source: Stewart Butterfield interviews

Fred Wilson / Union Square Ventures — Fred Wilson publicly regrets passing on Coinbase: 'We passed on it. That was a mistake.'

Source: Fred Wilson's blog

Multiple VCs — Social network for professionals before Facebook proved the social model — many VCs passed.

Source: Reid Hoffman interviews

Multiple VCs — Concerns about copyright liability from the DMCA. Sequoia invested. Google acquired for $1.65B.

Source: YouTube founding story

Multiple VCs — Browser-based design tool — VCs questioned why designers would use a web app instead of native software.

Source: Dylan Field interviews

Multiple VCs — YC partner Paul Buchheit nearly cut it from the batch. Many late-stage VCs underestimated food delivery TAM.

Source: Various

Multiple VCs — Same-day grocery delivery — VCs cited thin margins and Webvan's failure as reasons to pass.

Source: Various