In today's founder-centric climate, many VCs avoid confrontation to protect their reputation (NPS) within the founder network. This fear of being blacklisted leads them to abdicate their fiduciary duty to shareholders, failing to intervene even when a company's performance is dire and hard decisions are needed.

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.

David Cohen of Techstars advises founders to request references from a VC's failed investments. This reveals how an investor behaves during difficult times, providing a more honest assessment of their character and support level than speaking only with successful founders.

An investor's best career P&L winners are not immediate yeses. They often involve an initial pass by either the investor or the company. This shows that timing and building relationships over multiple rounds can be more crucial than a single early-stage decision, as a 'missed round' isn't a 'missed company'.

Duolingo's first investors admitted they didn't believe in the education market, which they considered a bad business. They invested solely because founder Luis von Ahn had a previous successful exit to Google, demonstrating that a founder's track record can be more persuasive to early VCs than the business idea itself.

DFJ Growth passed on a pre-revenue LinkedIn at a $1B valuation because they lacked a clear revenue signal. This highlights a common VC pitfall: over-indexing on current financial metrics and under-valuing powerful network effects and analogous, proven business models from other tech giants.

Bessemer Venture Partners publicly lists massive companies it passed on to foster a learning culture. This highlights their philosophy that the opportunity cost of missing a transformative company (a crime of omission) is far more damaging than investing in one that fails (a crime of commission).

Top VCs' biggest regrets come from passing on genuinely 'great' founders over solvable diligence issues. Mike Maples Jr. advises that when you encounter this rare trait, you should invest immediately, even if the business model is unclear.

VCs often pass on great companies by over-indexing on the theoretical threat of future competition from incumbents like Google. Andreessen Horowitz's post-mortems show this is a common mistake. The better approach is to invest in a founder's unique, "spiking strengths" rather than focusing on a lack of hypothetical future threats.