The most successful venture investors share two key traits: they originate investments from a first-principles or contrarian standpoint, and they possess the conviction to concentrate significant capital into their winning portfolio companies as they emerge.

When Peter Thiel fired Elon Musk from PayPal, he treated him well by fully vesting his stock. This preserved their relationship, leading Musk to later seek investment from Thiel for SpaceX. That decision could yield a $100B+ return for Founders Fund, showing how kindness can pay off.

Top growth investors deliberately allocate more of their diligence effort to understanding and underwriting massive upside scenarios (10x+ returns) rather than concentrating on mitigating potential downside. The power-law nature of venture returns makes this a rational focus for generating exceptional performance.

Contrary to the instinct to sell a big winner, top fund managers often hold onto their best-performing companies. The initial 10x return is a strong signal of a best-in-class product, team, and market, indicating potential for continued exponential growth rather than a peak.

The asymmetrical nature of stock returns, driven by power laws, means a handful of massive winners can more than compensate for numerous losers, even if half your investments fail. This is due to convex compounding, where upside is unlimited but downside is capped at 100%.

The standard VC heuristic—that each investment must potentially return the entire fund—is strained by hyper-valuations. For a company raising at ~$200M, a typical fund needs a 60x return, meaning a $12 billion exit is the minimum for the investment to be a success, not a grand slam.

Founders Fund invested nearly 10% of its fund into SpaceX immediately following a launch failure, betting on Elon Musk's team despite their lack of aerospace experience. This exemplifies a high-conviction, founder-centric investment thesis that ignores conventional industry wisdom and short-term setbacks.

The majority of venture capital funds fail to return capital, with a 60% loss-making base rate. This highlights that VC is a power-law-driven asset class. The key to success is not picking consistently good funds, but ensuring access to the tiny fraction of funds that generate extraordinary, outlier returns.

True alpha in venture capital is found at the extremes. It's either in being a "market maker" at the earliest stages by shaping a raw idea, or by writing massive, late-stage checks where few can compete. The competitive, crowded middle-stages offer less opportunity for outsized returns.