Many problems have a single "correct" answer (convergent). Investing is different; it's a "divergent" problem where key questions require balancing opposing virtues: concentration vs. diversification, patience vs. urgency. Success lies not in finding a single rule, but in intuitively harmonizing these tensions.

In high-inflation environments, stocks and bonds tend to move in the same direction, nullifying the diversification benefit of the classic 60/40 portfolio. This forces investors to seek non-correlated returns in real assets like infrastructure, energy, and commodities.

Owning multiple stocks or ETFs does not create a genuinely diversified portfolio. True diversification involves owning assets that react differently to various economic conditions like inflation, recession, and liquidity shifts. This means spreading capital across productive equities, real assets, commodities, hard money like gold, and one's own earning power.

The real benefit of diversification is matching assets with different time horizons (e.g., long-term stocks, short-term bills) to your future spending needs. All asset allocation is ultimately an exercise in managing financial goals across time.

BlackRock's CIO of Global Fixed Income argues that unlike equities, fixed income is about consistently getting paid back. The optimal strategy is broad diversification—tilting odds slightly in your favor and repeating it—rather than making concentrated, high-conviction "bravado" bets on specific market segments.

The sign of a working diversification strategy is having something in your portfolio that you're unhappy with. Chasing winners by selling the laggard is a common mistake that leads to buying high and selling low. The discomfort of holding an underperformer is proof the strategy is functioning as intended, not that it's failing.

Historical analysis of investors like Ben Graham and Charlie Munger reveals a consistent pattern: significant, multi-year periods of lagging the market are not an anomaly but a necessary part of a successful long-term strategy. This reality demands structuring your firm and mindset for inevitable pain.

Gold is a low-returning asset, similar to cash. Its primary value in a portfolio is not appreciation but diversification. During periods of stagflation or debt crises when other assets like stocks and bonds perform poorly, gold tends to do very well, stabilizing the portfolio.

Investor Mark Ein argues against sector-specific focus, viewing his broad portfolio (prop tech, sports, etc.) as a key advantage. It enables him to transfer insights and best practices from one industry to another, uncovering opportunities that specialists might miss.