To avoid confirmation bias and make disciplined capital allocation decisions, investors should treat every follow-on opportunity in a portfolio company as if it were a brand-new deal. This involves a full 're-underwriting' process, assessing the current state and future potential without prejudice from past involvement.

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'.

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).

The rationale behind backing Flow wasn't an oversight of past issues, but a deliberate strategy to invest in a founder with world-class, "spiking" strengths in brand building and company creation. This aligns with the firm's philosophy of prioritizing extreme strengths over a lack of weaknesses.

Redpoint's early-growth fund concentrates on Series B deals, entering after product-market fit is established but before explosive growth becomes apparent in the metrics. The strategy is to invest "a half step before something becomes obvious in the numbers," capturing value at a critical turning point.

Contrary to the belief that smaller VC funds generate higher multiples, a16z's data shows their larger funds can outperform. This is driven by the massive expansion of private markets, where significant value is now created in later growth stages (Series C and beyond).

A primary function of Andreessen Horowitz's growth fund is to correct errors of omission from its early-stage team. Joking referred to as the "fix the mistake fund," it provides a second chance to invest in companies the firm initially passed on. This internal synergy is a core part of their multi-stage strategy.

A16z's growth fund avoids traditional investment committees, which can lead to politicization and slow decisions. Instead, it uses a venture-style "single trigger" model where one partner can champion a deal, encouraging intellectual honesty and speed.

The most critical decision in venture isn't the final investment vote but the mid-funnel choice of which companies get a deep look. The costliest errors are false negatives—great companies dismissed prematurely. Firms should therefore optimize process hygiene at this stage, implementing mandatory post-meeting debriefs to avoid these misses.