Complimentary Book

Complimentary Book:The Power Of Zero: a playbook for getting into the 0% tax bracket, especially in retirement

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Insights

Read The Course First.

Plain-English guides to the tax questions high earners ask most. Written by Tyler Ostrovsky, sourced to the IRS and the tax code, and worth reading before you ever book a call.

Featured Guide · 6 Min Read

The Second Bill: The Tax Bill High Earners Often Don't Plan For

The Second Bill is the income tax that comes due when money leaves a pension, cash balance plan, traditional 401(k) or IRA. The deduction you took on the way in postponed that tax to a later year. How large the bill turns out to be depends mostly on when the money comes out, who takes it out and what else they earn that year, which is why it rewards planning long before the first withdrawal.

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The Library

Each guide answers one question properly, then points you to the calculator or conversation that fits.

  1. Athletes Financial Planning Considerations During A Professional Athlete's Peak Earning Years A short, uneven, top-bracket career creates planning problems most earners never face. Taxes, liquidity, protection, the transition and how to coordinate the team. 5 min read
  2. Business Owners How Business Owners Can Coordinate Tax Planning With Their CPA Your CPA files the return. Planning happens months earlier. A practical calendar for owners, the questions worth raising, and how a strategist fits in. 4 min read
  3. Estate Planning The $15 Million Estate Tax Exemption: What Changed In 2026, And What Still Catches Families Out The federal estate tax exemption is $15 million per person in 2026. What that means for married couples, why growing estates still cross the line, and what to review. 4 min read
  4. Tax Strategy What Is Tax Diversification, And Why Does It Matter? Taxable, tax-deferred and tax-free money are taxed on different schedules. Why the mix matters as much as the total, and how high earners end up lopsided. 4 min read

Your Tee Time Is Open.

Thirty minutes with Tyler. You leave with a clear read on your tax exposure and which strategies fit your situation.

  • 30 minutes on Zoom
  • No preparation needed
  • Bring your CPA or spouse if you like
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