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.

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.

The "Liking-Loving Tendency" causes investors to identify personally with their holdings. They ignore faults, favor associated things, and distort facts to maintain positive feelings. This emotional attachment leads them to rationalize bad news and hold deteriorating assets for too long, destroying capital.

Effective due diligence isn't a checklist, but the collection of many small data points—revenue, team retention, customer love, CVC interest. A strong investment is a "beam" where all points align positively. Any misalignment creates doubt and likely signals a "no," adhering to the "if it's not a hell yes, it's a no" rule.

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 founder must simultaneously project unwavering confidence to rally teams and investors, while privately remaining open to any evidence that they are completely wrong. This conflicting mindset is essential for navigating the uncertainty of building a startup.

A common mistake in venture capital is investing too early based on founder pedigree or gut feel, which is akin to 'shooting in the dark'. A more disciplined private equity approach waits for companies to establish repeatable, business-driven key performance metrics before committing capital, reducing portfolio variance.

The common bias of loss aversion doesn't affect investors who have done exhaustive upfront work. Their conviction is based on a clear understanding of an asset's intrinsic value, allowing them to view price drops as opportunities rather than signals of a flawed decision.

In 2008, Howard Marks invested billions with conviction while markets crashed, yet he wasn't certain of the outcome. He held the paradox of needing to act decisively against the crowd while simultaneously accepting the real possibility of being wrong. This mental balance is crucial for high-stakes decisions.