DIY Financial Planning
Your financial future, guided by market history, powered by math, shaped by insight.
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Most investors think portfolio construction is mainly about asset allocation. But there is another layer hiding underneath: The mechanism that determines how portfolio weights evolve over time. Two portfolios can own nearly identical assets and still produce materially different long-term…
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The Hidden Cost of “Just Buy VT”
For years, the default advice for global equity investing has been simple: buy a total-world index fund and leave it alone. Funds like Vanguard Total World Stock Index Fund ETF Shares are designed to provide broad global diversification in a…
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Portfolio Backtesting Tool (1970 – present) with Full Asset Class Coverage
Most portfolio backtesting tools are constrained in ways that matter most: access to limited number of asset classes, short backtesting time span or both. To address these constraints, PrincetonAsset aggregates data from multiple sources into a portfolio backtesting tool that…
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The Curious Case of OBBBA Tax Savings
The 2025 One Big Beautiful Bill Act (OBBBA) reform was intended to make one of the biggest changes to Social Security taxation in decades. Most commentary focuses on the headline feature – eliminating the taxation of Social Security benefits for…
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Tax Gain Harvesting: Extreme Caution at Long Horizons
Many investors have heard of tax-loss harvesting, but its lesser-known cousin – tax gain harvesting (TGH) – is often misunderstood. While it might sound appealing to sell appreciated assets to reset your cost basis, the reality is that: over long…
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IRS Notice 2022-6: Missing Annuity Payment-Timing Convention Creates Systemic 72(t) Penalty Risk
We submitted this letter to the Taxpayer Advocate Service (TAS) systemic issue reporting process, a legitimate, formal channel to bring this problem to the attention of the IRS The ambiguity in IRS Notice 2022-6 regarding the payment timing, annuity-immediate (end-of-year)…
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PSA: we tested the top 6 “72(t) calculator” results on Google. All of them fail the IRS’s own reference examples.
If you’re planning early retirement with a 72(t) SEPP distribution, you need accurate calculations. We researched the topic and discovered that every popular calculator we tested produces incorrect results when compared to the IRS’s own published examples. The IRS Reference…
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Understanding 72(t) SoSEPP Distributions
For many investors, tapping retirement funds before age 59½ normally means a 10% early withdrawal penalty. But the IRS provides us with an exception: Sequence Of Substantially Equal Periodic Payments (SoSEPPs) under IRC §72(t). If you follow the rules carefully,…
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How Roth Conversions Affect ACA and IRMAA Subsidies
When planning a Roth conversion, it’s easy to focus only on the income tax impact. But if you’re on ACA health insurance or Medicare, the conversion can also trigger changes in your ACA subsidies and IRMAA surcharges. In this example,…
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A Guide to U.S. Income Categories for Tax Planning
When it comes to tax planning, not all income is created equal.Two people could both “earn” $100K a year and still end up paying very different amounts in federal and state taxes – simply because of what type of income…
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