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.

A successful, high-volume angel investing strategy doesn't rely on the difficult task of picking the few massive winners. Instead, the job is to effectively filter out the obvious non-starters. This process of elimination creates a diversified portfolio of pre-vetted, high-potential companies, effectively indexing the top tier of the ecosystem.

For a venture capital fund, the costliest error isn't investing in a startup that fails (a sin of commission); it's passing on one that becomes a massive success (a sin of omission). This fear drives a high-volume sourcing strategy that prioritizes seeing every potential deal.

In venture capital, a portfolio with no failed investments is a sign of a flawed, risk-averse strategy. The goal isn't to avoid losses but to back the market leader in a potentially huge category. Losing money on the leader if the entire category fails is an acceptable and expected outcome.

The most painful investment misses—the 'anti-portfolio'—can serve as the primary inspiration for a new venture firm's strategy. Nnamdi Okike of 645 Ventures used his experience passing on companies like Skype and Facebook to build a new firm specifically designed to identify and invest in similar opportunities.

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).

New VCs often rush to make deals to prove themselves, but this leads to a portfolio of mediocre companies. These investments consume a disproportionate amount of time and energy, leaving no bandwidth to pursue the truly exceptional, career-making opportunities that may appear later.

Contrary to the popular debate, venture is primarily an access game, not a picking game. The core challenge is building a system to see a high volume of exceptional founders and then win the allocation. Once that is achieved, selecting which ones to back becomes straightforward.

Bessemer Venture Partners maintains a public 'anti-portfolio' of massive companies like Tesla and Atlassian that they passed on. This practice serves as a constant reminder to learn from their 'crimes of omission' and demonstrates respect for the entrepreneurs they say 'no' to.