Missing successful startups is a necessary evil for venture capitalists. According to veteran VCs, not having an anti-portfolio suggests an investor isn't seeing enough high-quality opportunities. It's a painful but essential sign of being active in the market.
Investor Glenn Solomon backed out of leading Airbnb's Series A after founder Brian Chesky rejected the request for a board seat. Chesky's signal that he 'didn't want help' from his lead investor was a significant factor in the multi-billion dollar decision to pass.
A founder passed on acquiring a prediction aggregator, a business he believed was central to his company's mission. He hesitated because he felt he lacked the credibility to make such a bold move his 'main thing,' a decision he now views as a significant missed opportunity.