I failed 22 times... then I built a $2.5B Company

TL;DR

Christina Cacioppo quit her job at USV, taught herself to code over two years, built ~35 projects that failed, then founded Vanta (security/compliance for startups) which reached a $2.45B valuation. The core message: don't count yourself out after repeated failure; the majority of creative work is just learning to make the small fraction that soars; managing your own psychology and testing the ris

Key insights

• The "right side" of an email (e.g., @usv.com) gives institutional power; quitting that to bet on the "left side" (your name) is a high-risk move that most people advise against.
• Fred Wilson advised Christina to either "fake it till you make it" or pick a niche and go deep; he told her she wasn't suited for faking it, so she should specialize (he suggested crypto in 2012).
• Christina built the book-discovery site for herself despite knowing it was not a business – she did it to have a personally meaningful coding project that forced learning (e.g., CSS animations).