Tax Strategy Guides 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.
The Short AnswerThe 19th Hole Financial library is a set of plain-English guides by Tyler Ostrovsky on the tax questions high earners ask most, from the Second Bill on retirement accounts to the 2026 estate tax exemption. Every figure is sourced to the IRS and the tax code.
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.
Read The GuideThe Library
Each guide answers one question properly, then points you to the calculator or conversation that fits.
- Tax Strategy Tax Planning For Physicians In Ventura County: The Questions To Bring To Your CPA California's 12.3% top rate and 1% surcharge over $1,000,000, the 3.8% investment income tax and the 2026 plan limits, framed as questions for your CPA.
- Retirement Income Required Minimum Distributions: The Withdrawals That Start On A Schedule When RMDs start, how the Uniform Lifetime Table sets the amount, how California treats them, the 25% penalty for missing one and which accounts have none.
- Retirement Income How Much Tax Will You Owe On 401(k) Withdrawals In Retirement? A California Example How pre-tax 401(k) withdrawals are taxed by the IRS and California, with a worked example for a married Ventura County couple drawing $150,000 to $400,000 a year.
- Business Owners Selling A Business In Ventura County: What The Tax Bill Looks Like In 2026 Federal capital gains, the 3.8% net investment income tax and California tax on a business sale, with a $5,000,000 example taken in one year or over five.
- Business Owners We Read 18,461 Small-Business Pension Filings. Here Is The Tax Waiting On The Way Out. Every 2024 federal filing for a small defined benefit plan costing $100K+ a year: $63.3 billion across 18,453 businesses, and the tax waiting on the way out.
- 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.
- 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.
- 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.
- 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.
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