Fintech fund Santana Growth passed on successful challenger banks because they deemed the segment unattractive and highly competitive. They admit underestimating how strong execution could allow certain teams to succeed against the odds, navigating a 'narrow line' to a successful outcome in a tough market.
True Ventures passed on Uber's seed round because it was a 'project' without a dedicated leader. This demonstrates how a disciplined investment thesis, in this case requiring a 'visionary leader,' can cause a pass on a massive winner but also provides a consistent framework for decisions and peace of mind.
Blue Moon passed on Perplexity's $90M round due to strict price discipline and lack of time for deep diligence. This highlights how rigid adherence to valuation can lead to missing out on category-defining companies, especially in rapidly evolving markets like early AI where standard metrics may not apply.