The worst feeling for an investor is not missing a successful deal they didn't understand, but investing against their own judgment in a company that ultimately fails. This emotional cost of violating one's own conviction outweighs the FOMO of passing on a hot deal.

To truly understand a potential financial partner, the Chomps team went beyond the supplied references. They found a founder whose company didn't succeed under the PE firm's investment. His positive review of the partner's character, despite the negative outcome, provided the most powerful signal of trust.

True investment courage isn't just writing the first check; it's being willing to invest again in a category after a previous investment failed. Many investors become biased and write off entire sectors after a single bad experience, but enduring VCs understand that timing and team make all the difference.

Post-mortems of bad investments reveal the cause is never a calculation error but always a psychological bias or emotional trap. Sequoia catalogs ~40 of these, including failing to separate the emotional 'thrill of the chase' from the clinical, objective assessment required for sound decision-making.

A near-bankruptcy experience instilled in Ed Stack an aversion to debt. This "paranoid" financial discipline, while criticized by Wall Street as suboptimal, became a key strategic advantage. By self-funding growth, Dick's maintained control and agility, allowing it to survive downturns that crushed its highly-leveraged competitors.

Orlando Bravo's first deals as a young PE professional were a catastrophe, with two going to zero. His mentor, Carl Thoma, gave him a second chance but with a crucial lesson: you can make mistakes, but you cannot make the same *type* of mistakes again.

Seemingly costly failures provide the unique stories, data, and scars necessary to teach from experience. This authentic foundation is what allows an audience to trust your guidance, turning past losses into future credibility.

Instead of dismissing harsh criticism, extract the underlying truth. A brutal investor rejection focused Gamma on intertwining product and growth from the very beginning, acknowledging the difficulty of competing against incumbents. This became a foundational part of their strategy.

Contrary to advisors who predicted EHRs would quickly fix healthcare data, Matt Holt invested in HealthPort, believing the system's deep brokenness provided a 15-20 year runway. The insight is that intractable, systemic fragmentation creates durable opportunities for foundational infrastructure players.