Jeff Bussgang of Flybridge had a "won" deal with Viva on a Friday, only to lose it by Monday. As a Boston/New York firm chasing a hot deal in Silicon Valley, they were at a geographical disadvantage against a local firm, who ultimately led the highly successful Series A round.
Paul Madera of Meritech passed on Palantir four times. Despite being introduced early, his firm repeatedly concluded the price was "out of line," causing them to miss what became the highest multiple software company. This shows how strict valuation discipline can blind investors to category-defining outliers.
Investor Victor Orlovski writes 10-15 pages of notes when he passes on a company, compared to only 5-6 pages for an investment. This disciplined reflection on "anti-portfolio" decisions allows him to analyze his reasoning, identify biases, and improve his investment judgment over time.
An investor passed on Chime's seed round despite a strong founding team. The reason: he personally thought the product "makes no sense" and couldn't see himself building it. This illustrates a common early-stage trap where VCs substitute their own product ideas for the founder's vision, rather than betting on the team.