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  2. Cullen Roche on the Art of Building a Perfect Portfolio
Cullen Roche on the Art of Building a Perfect Portfolio

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots · Jan 12, 2026

Portfolio expert Cullen Roche reveals why standard models fail and how to build *your* perfect portfolio by matching assets to your unique liabilities.

Standard Risk Questionnaires Fail Because Investors Confuse Rationality with Reality

Investors consistently overestimate their risk tolerance on questionnaires because they know the "correct" answer. However, during an actual crisis, fear feels entirely rational and justified, leading them to panic and sell despite their stated intentions.

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

Asset Booms Pull Future Returns into the Present, Increasing Downside Risk

When an asset sees a massive price surge, it's effectively a "price compression" that pulls years of expected returns into a short period. This raises the probability of future volatility or stagnant performance, as the future gains have already been realized.

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

"Buy the Dip" is Impractical Advice; Crises Erode Both Portfolios and Incomes

The best times to invest, like market bottoms during a crisis, often coincide with peak personal financial instability, such as job loss. This makes the common advice to "buy the dip" or "hold on" practically impossible for many, beyond just behavioral challenges.

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

A "Forward Cap" Portfolio Weights Assets Based on Future Macro Trends, Not Current Size

Instead of using current market-cap weightings, a "forward cap" strategy allocates capital based on extrapolated macroeconomic trends. This means overweighting a sector like tech based on its projected future dominance, essentially "skating to where the puck is going."

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

Big Tech's Dominance Defies Investing Rules by Combining Size with High Growth

Big Tech's sustained outperformance presents a portfolio anomaly. These companies are simultaneously the largest market components and among the fastest-growing, a rare combination that breaks historical patterns where size implies maturity and slower growth, forcing managers to adapt.

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

The Boglehead Portfolio's Elegant Simplicity Is a Flaw in Correlated Downturns

While lauded for its simplicity, the three-fund Boglehead portfolio reveals a key weakness in environments like 2022. Its lack of exposure to truly uncorrelated assets like cash means investors suffer when its core components fall in unison. A portfolio can be "too simple."

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

Model Your Future Income as a Bond to Better Calibrate Portfolio Risk

Your human capital—your future earning potential—should be treated as a fixed-income asset in your total portfolio. A stable, high-value income stream acts like a large bond holding, providing the behavioral and financial capacity to take significantly more risk with your investment assets.

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

Truly Passive Investing is a Myth; The Global Market Portfolio is Uninvestable

A truly passive portfolio would own all global financial assets in proportion to their market value. However, this is impossible because many assets, like government-held bonds or restricted foreign stocks, are not available to public investors, making every real-world index fund an active bet.

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago

The 60/40 Portfolio Was Born From Surviving, Not Thriving, in the Great Depression

The popular 60/40 stock-bond split traces its roots to the Wellington Fund during the 1929 crash. Its heavy bond allocation meant it was "crushed way less" than all-equity peers. Its fame grew not from high returns but from superior relative performance during a catastrophe.

Cullen Roche on the Art of Building a Perfect Portfolio thumbnail

Cullen Roche on the Art of Building a Perfect Portfolio

Odd Lots·a month ago