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Portfolio construction

Portfolio construction

A trip to Monte Carlo

I’ve been messing around with the Testfol.io Monte Carlo Simulator. The free tier is pretty crippled — 500 simulations, 15-year cap — but Testfol.io is literally the only place where we have a decent Trend Following proxy that actually goes back decades. Thirty-eight years of data isn’t exactly blowing my Read more

By TheItalianLeatherSofa, 1 weekMay 9, 2026 ago
Portfolio construction

No Diversification

On Wall Street, no one ever says “okay, enough is enough.” The mentality is always “if a little bit is good then a lot is better. And if a lot is better then way more is great!” Usually, people have to lose a lot of money before this wears off. Read more

By TheItalianLeatherSofa, 2 monthsMarch 21, 2026 ago
Portfolio construction

Portable Alpha: a Primer

Three years ago, I moved into this incredibly well-placed and reasonably priced apartment in Zurich. Then I started this podcast nonsense, which brought a problem along: it made me crave a home office…while I also need a bed. In the physical world, we’re constrained by the floor space. If I Read more

By TheItalianLeatherSofa, 3 monthsFebruary 15, 2026 ago
Personal Finance Portfolio construction

Total Portfolio Approach

In the world of finance, we are largely taught to worship at the altar of the Law of Large Numbers. The theory is simple: over a long enough time horizon, your investment outcomes will eventually converge toward the historical average. But there’s a problem. You aren’t an “average.” You aren’t Read more

By TheItalianLeatherSofa, 3 monthsFebruary 4, 2026 ago
Portfolio construction

All Weather Portfolio Lab

Roger Nusbaum recently published an excellent piece. And, in the spirit of efficient markets, I’ve decided to steal his title as well. While Roger focused on how to size alternative assets, I believe that’s a secondary concern. The data suggests that the most critical decision isn’t the weight: it’s the Read more

By TheItalianLeatherSofa, 4 monthsJanuary 16, 2026 ago
Portfolio construction

The Diversification Trap

Almost two years ago, I wrote about why diversification isn’t a free lunch. Now, I’m watching everyone pile into gold, and I need to say something. Me that four years ago, inspired by PortfolioCharts, wrote this about gold. But that was back then, when nobody cared. Today? Everyone’s buying it. Read more

By TheItalianLeatherSofa, 6 monthsNovember 5, 2025 ago
Portfolio construction

Stacking, Diversifiers and Responders

A very kind reader sent me the link to a paper aimed to show the wonders this portfolio: The portfolio for the apocalypse 😉 Simple and systematic. While there isn’t much to say about the portfolio first two component, I will summary here the tail hedging strategy: systematically purchase 10-delta Read more

By TheItalianLeatherSofa, 7 monthsOctober 28, 2025 ago
Personal Finance Portfolio construction

Retirement Spending Rules

“How much income can I count on from my retirement savings?” With traditional pensions, defined benefit plans, becoming as rare as a good plumber, most of us are stuck figuring this out on our own. The math here is brutal. You don’t know how long you’ll live. You don’t know Read more

By TheItalianLeatherSofa, 7 monthsOctober 13, 2025 ago
Personal Finance Portfolio construction

Why Your Brain Hates Good Investment Strategies

On social media, I read many critiques of managed futures strategies…also from people I consider intelligent. These posts got me thinking about a fundamental tension in investing: some of the strategies that work best mathematically are often the hardest to stick with emotionally. The Torture of Positive Skew Managed futures Read more

By TheItalianLeatherSofa, 8 monthsSeptember 27, 2025 ago
Personal Finance Portfolio construction

FIRS – The FIRE Funds Wealth Builder ETF

I found this ETF reading Roger Nusbaum blog. When I first saw the name and website, I instantly dismissed it as a marketing stunt. But Roger continued to mention it, so one day I bit the bullet and dug more. INVESTMENT APPROACHThe Adviser allocates the Fund’s portfolio equally among four Read more

By TheItalianLeatherSofa, 8 monthsSeptember 11, 2025 ago

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