LEDGER4,2001,8406,040Roth ConversionSCHEDULE D — CAPITAL GAINSLOSS: $(2,340.00)Adjusted basis: $18,200$1k$5k$10k7,842.50-12+8-4+22=14← compound effecttax-loss harvesting ↑cost basisL
Vol. I · No. 1 · Feb 2026
Personal Finance · Monthly Edition
A monthly publication

Compound interest one month. Tax-loss harvesting the next. Each issue a carefully folded broadsheet — patient as a long letter, precise as a balance sheet.

For those who read the footnotes.4,200 subscribers
§ Editorial Vision

Depth defeats frequency.

here are already ten thousand newsletters that tell you what happened. Ledger tells you why it matters, how it works, and what to do about it — one subject at a time, with the space to get it right.

We spend four weeks on a single topic. We read the IRS publications, the academic papers, the court cases. We talk to the CFP who has run the numbers and the freelancer who made the mistake. Then we write it once, clearly, at the length it actually requires — never shorter for convenience, never longer for authority.

"One issue. 4,000 words. No ads, no affiliate links, no sponsored content. Just the subject, exhausted."

By the numbers
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Subscribers
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4,000
Words per issue
Avg. 18 min read
100%
Editorially independent
No sponsors, ever
26
Issues published
Archive available
From the style guide
§

Every claim cites a primary source.

Dollar figures are inflation-adjusted to current year.

Tax advice is educational, not professional counsel.

Corrections are published in the following issue.

Written for

Early-career professionals who maxed their first 401(k)

Mid-life couples who want to understand their mortgage, not just sign it

Self-employed freelancers with no CFO but themselves

II
§ Sample Issues

Three issues. Three proofs.

Click any issue to see the full table of contents. Every archive issue is available to subscribers.

Open financial journal with handwritten calculations and a fountain pen resting on the page
No. 12
October 2025

The Compound Effect

Why time is the only variable that can't be bought

Words4,340
Read19 min

The number that will appear on your retirement statement in 2048 is not primarily a function of how much you earn. It is a function of when you start and whether you stop.

  1. 01The mathematics of patience
  2. 02Why your 401(k) statement lies to you
  3. 03Reinvestment: the invisible engine
  4. 04Tax drag and how to minimize it
  5. 05The 40-year model: three scenarios
  6. 06Behavioral traps that kill compounding
Closeup of financial charts and graphs on paper with a pencil marking annotations
No. 18
April 2025

Tax-Loss Harvesting

Converting paper losses into real tax savings

Words4,890
Read22 min

Selling a losing position is not defeat. When done deliberately, it is one of the few legal mechanisms for manufacturing a tax asset from a market setback.

  1. 01What a realized loss actually means
  2. 02The wash-sale rule, fully decoded
  3. 03Harvesting across account types
  4. 04When NOT to harvest (the math)
  5. 05Automated harvesting: pros and cons
  6. 06Year-end vs. opportunistic timing
Stack of financial documents and forms with a red wax seal on an envelope
No. 23
September 2025

The Backdoor Roth

A legal workaround for high-income earners

Words4,120
Read18 min

The backdoor Roth is not a loophole in the pejorative sense. Congress created the conversion mechanism deliberately. Using it is not tax avoidance — it is tax literacy.

  1. 01Why the income limit exists
  2. 02The two-step conversion, step by step
  3. 03The pro-rata rule: the trap nobody mentions
  4. 04Mega backdoor: employer plan version
  5. 05Roth conversion ladders for early retirement
  6. 06Paperwork: Form 8606 explained
Portrait of Marcus Holloway, founder and editor of Ledger, wearing glasses and a thoughtful expression
Ed.
Marcus Holloway
Founder & Editor
CFP® Certificant
Former tax attorney, 2009–2018
CFA Level II candidate
Teaches personal finance at community college
Methodology

Every issue cites primary sources: IRS publications, SEC filings, peer-reviewed research, and named practitioners. No anonymous sources. No sponsored claims.

§ A Note from the EditorFebruary 2026

started writing Ledger because I kept having the same conversation. A friend would call — a nurse, a software engineer, a freelance photographer — and they'd ask about something they'd read. A backdoor Roth. Sequence-of-returns risk. The step-up in basis at death. Smart people. Good questions. And nowhere to read a real answer.

Financial media has two modes: the 800-word article that leaves out every important caveat, and the 400-page textbook that assumes you already know what a basis point is. Ledger lives in the space between. Long enough to be honest. Short enough to finish.

"I will never publish an issue I wouldn't hand to my own mother and say: this is the whole picture."

Each issue takes four weeks to write, fact-check, and edit. The topic is chosen because it's genuinely useful to the three people I picture when I write: the 29-year-old who just got their first brokerage account, the 47-year-old refinancing their second home, and the 38-year-old freelancer filing quarterly for the first time.

If you read the free sample and it's not what you were looking for, I'd genuinely like to know. The email address is real and I read every reply.

Marcus Holloway
Founder, Ledger
IV

"The backdoor Roth issue saved me from a $4,200 pro-rata tax bill I didn't know I was walking into."

Priya NairSoftware engineer, 31

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James OkaforNurse practitioner, 34

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"The writing doesn't condescend. It assumes you're intelligent and just haven't had the right explanation yet."

Rachel OkonkwoHigh school teacher, 42

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