Ron Conway — portfolio autopsies

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

Amazon for the price-sensitive: $1 items shipped free, no questions asked

Discount marketplace IPO'd at $14B then sold for $173M three years later

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

Digital media startup fabricated metrics — CEO impersonated YouTube's CEO

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

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

Mapped every deal relationship in the enterprise — except the one that would buy them out.

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

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

A/B testing pioneer sold for a fraction of its valuation after free tools ate the market

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

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

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.

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

Kevin Rose built a better Twitter with file sharing. Two weeks after acquisition, it was gone.