Ashton Kutcher — portfolio autopsies

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 $176M AGI startup backed by Elon Musk and Jeff Bezos — acquired by Amazon for the engineers, not the AI.

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

On-demand laundry pickup proved that dry-cleaning economics can't support a tech company

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

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

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

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