Privat Capital holds a concentrated portfolio of 16-17 stocks. This strategy forces deep conviction in each position and ensures that winners have a meaningful impact on fund performance. Over-diversification can dilute both research focus and the potential returns from a fund's best ideas.

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.

Analysis of Keynes's portfolio reveals a subtle skill: his true value-add came from ensuring his lowest-conviction ideas received minimal capital. Over his career, his bottom five positions shrank from 11.7% to just 6% of his portfolio, demonstrating a disciplined approach to managing risk on less-certain bets.

Instead of making large initial bets, a more effective strategy is to take small, "junior varsity" positions. Investors then aggressively ramp up their size only when the thesis begins to demonstrably play out, a method described as "high conviction, inflection investing."

Many investors wrongly equate high conviction with making a large initial investment. A more evolved approach is to start with smaller at-cost positions, allowing a company's performance to earn its eventual large weighting in the portfolio. This mitigates risk and improves decision-making.

Even with big wins, a venture portfolio can fail if not constructed properly. The relative size of your investments is often more critical than picking individual winners, as correctly sized successful investments must be large enough to overcome the inevitable losers in the portfolio.

Since it's impossible to know upfront which investments will generate outlier returns, the key isn't picking them but holding them. The biggest mistake is 'cutting your flowers to water your weeds'—selling winners to invest in underperformers. You must 'circle the wagons' around your core assets.

Allocate more capital to businesses with a highly predictable future (a narrow "cone of uncertainty"), like Costco. Less predictable, high-upside bets should be smaller positions, as their future has a wider range of possible outcomes. Conviction and certainty should drive allocation size.

Analysis of New Zealand Super's performance revealed a mediocre "batting average" (hit rate of successful investments) but an amazing "slugging average." They succeeded by allocating disproportionately large amounts of risk to their highest-conviction ideas. The magnitude of wins, not their frequency, drives long-term outperformance.