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Sunday, Feb 23, 2026

Compound — A Sunday Letter

The Only Financial Letter That Respects Your Spreadsheet.

Index funds, tax-loss harvesting, and geographic arbitrage — distilled into one calm, considered read. Delivered every Sunday morning before the market opens.

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Featured Issue
47
Issue No. 47Tax Strategy

The Roth Conversion Ladder: Why Physicians Earning $380K Are Quietly Moving Money Backward to Retire Forward

here is a peculiar arithmetic to the Roth conversion ladder that most financial advisors gloss over — not because it's complicated, but because it requires patience that contradicts their business model. The strategy asks you to pay taxes now, deliberately, on money you've already sheltered, so that a decade from now, your withdrawals arrive tax-free at precisely the moment your marginal rate matters most.

For the physician earning $380,000 in attending salary who plans to step back at 52, the math resolves cleanly: five years of conversions, beginning the year after your last W-2, moving $60,000–$80,000 annually from traditional IRA to Roth while your income sits in the 22% bracket. The window is narrow. The savings are not.

"The window between your last paycheck and RMD age is not a gap — it is the most valuable financial real estate you will ever own."

— Compound, Issue 47

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Recent Issues
46
Issue No. 46Portfolio Design

Geographic Arbitrage, Quantified: The Spreadsheet Behind 14 CoastFIRE Relocations

When the dual-income couple in San Francisco runs the numbers on Medellín, the first figure that surprises them isn't the cost of living — it's the tax treaty. Colombia's bilateral agreement with the United States contains a provision that most expat forums have never discussed, one that effectively reduces the effective rate on passive income for US persons who establish genuine residency. We built the model. The results were not subtle.

"A $2.1M portfolio that barely covers San Francisco expenses becomes a 4.2% withdrawal rate in Lisbon — and a 3.1% rate in Chiang Mai."

Feb 16, 2026
45
Issue No. 45FIRE Math

Your 401(k) Is Not Your Retirement Plan. It Is One Instrument in an Orchestra You Have Not Yet Assembled.

The engineers who reach out to us most often are the ones who have done everything correctly — maxed the 401(k), opened the backdoor Roth, kept the expense ratio below 0.05% — and still feel a low-grade unease about whether it's enough. It usually isn't a math problem. It's a sequencing problem. The instruments are there. The arrangement is missing.

"Sequence-of-returns risk destroys more retirements than market crashes. The difference is that one feels like bad luck, and the other feels like bad timing."

Feb 9, 2026
From the Readership
"
I've been maxing my 401(k) for six years and thought I understood tax-advantaged accounts. Issue 41 on the mega backdoor Roth changed my entire sequencing strategy. The worked example alone was worth a year of subscriptions.
PV

Priya Venkataraman

Senior Staff Engineer · Seattle, WA

CoastFIRE target: $1.8M by 43

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The Archive

Forty-seven issues. One through six are below. The rest are waiting for you.

44
Tax Strategy7 min

Issue 44

Tax-Loss Harvesting at Scale: When the Wash-Sale Rule Becomes Your Biggest Risk

Feb 2, 2026Read →
43
Life After Work12 min

Issue 43

What Happens to Your Identity When the Attending Salary Stops

Jan 26, 2026Read →
42
Portfolio Design8 min

Issue 42

The Three-Fund Portfolio Is Not Boring. It Is the Endgame.

Jan 19, 2026Read →
41
FIRE Math10 min

Issue 41

Mega Backdoor Roth: The $46,500 Move Most 401(k) Plans Hide in Plain Sight

Jan 12, 2026Read →
40
Tax Strategy9 min

Issue 40

The Qualified Opportunity Zone: What the Tax Code Offers That Your Advisor Forgot to Mention

Jan 5, 2026Read →
39
Portfolio Design6 min

Issue 39

Year-End Rebalancing Is Not a Ritual. It Is a Decision Framework.

Dec 29, 2025Read →

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