Vol. 01 · Issue 04

The Smart Money — Weekly personal finance dispatches

Personal finance for people who want to be great with money — written by the friend who already is.

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Now openDesk 03 of 09

The Tax Desk.

Bracket management, entity structure, timing moves, and the handful of deductions civilians consistently miss — from a CPA who thinks in twelve-month cycles.

The framework

Tax planning is a twelve-month sport.

Most people meet their tax bill in April. That's exactly six months too late. Every dollar of good tax planning lives in the decisions you make before December 31.

  1. 01

    Bracket Awareness

    Know your marginal rate the way you know your zip code.

    Every big financial decision — Roth conversion, capital gain, bonus timing — is a bracket question in disguise.

  2. 02

    The Entity Question

    Sole prop, LLC, S-corp — the right one quietly compounds for a decade.

    Wrong at $50k is cheap. Wrong at $250k is a five-figure annual mistake.

  3. 03

    Timing Moves

    The same dollar of income or deduction is worth wildly different amounts in different years.

    Accelerate, defer, or bunch. The calendar is a tool, not a constraint.

  4. 04

    The Audit-Proof Standard

    Every clever position has to survive a bad day at the IRS.

    If it only works when nobody's looking, it doesn't work. Aggressive is fine. Fragile is not.

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