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

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FAQ

Straight Answers.

The questions high earners ask most, answered in the first sentence.

Working With Tyler

Who is 19th Hole Financial for?

Business owners, professional and retired athletes, physicians and executives earning $500,000 or more a year, and families with a large pre-tax retirement balance or an estate near the federal exemption. Below that income level most advanced strategies do not pencil out, and Tyler will say so on the first call.

What happens in the first conversation?

It is a 30-minute Zoom call. Tyler asks about your income, what you already have and what you want your money to do, then tells you plainly whether advanced planning is worth a closer look. No preparation is needed and nothing is sold on the first call. See all five steps.

Do I need to replace my CPA or financial advisor?

No. Tyler works alongside the professionals you already trust. Your CPA remains your CPA and your attorney remains your attorney; Tyler brings the strategy and insurance design, and they review it before anything is filed or signed.

Can my spouse, CPA or attorney join the meetings?

Yes, and it usually makes the planning better. Forward the Zoom invitation to anyone you want in the room, whether a spouse, CPA, attorney, agent or business manager.

Is this tax or legal advice?

No. Tyler is a licensed insurance agent, not a CPA or attorney. He designs tax strategy and insurance solutions and coordinates them with your CPA and attorney, who give the tax and legal sign-off.

Is my information kept private?

Yes. Conversations are one-to-one and confidential. The calculators on this site run in your browser; the numbers you type are not sent to us, and are saved only in your own browser so you do not lose them.

What happens in the five meetings?

The five meetings are named after a round of golf. Pre-Round Discovery is the first 30-minute conversation. Course Assessment reviews the documents you share and fills the gaps. The Turn delivers your Tax Advantage Scorecard and game plan. Back Nine activates the plan with your CPA and attorney. The 19th Hole covers onboarding once approved and ongoing reviews as things change. You decide at every step whether to continue.

Does Tyler work with clients outside California?

Tyler is based in and licensed in California, and most clients live there. The first conversation is on Zoom and many strategies are federal, so ask on the call; any insurance recommendation outside California is only made where Tyler holds the required license.

Can I refer a friend, client or teammate?

Yes. Most of Tyler's clients arrive through a referral from a client, a CPA or a teammate. Send an introduction here; Tyler reaches out personally and keeps it low-key.

Taxes For High Earners

What is the Tax Advantage Scorecard?

The Tax Advantage Scorecard is the report you receive in the third meeting, The Turn. It shows your tax bill today, the tax waiting in your retirement accounts and your estate exposure side by side, then the game plan that brings those numbers down. You can preview the idea with the free Tax Scorecard calculator.

Is Tyler Ostrovsky really a former professional golfer?

Yes. Tyler turned professional in 2012, as his official PGA Tour player profile shows, and played for eight years, with full status on PGA Tour Canada in 2014 and partial status in 2016. Before that he was a three-time All-Patriot League golfer at Lafayette College. Read his story.

How do the calculators work?

Each calculator applies published 2026 federal tax figures (and the latest published California brackets where relevant) to the numbers you enter, and lists its assumptions under the results. They are illustrative estimates for education; your CPA should review any result before you act on it.

How much tax will I pay when I take money out of my 401(k) or pension?

Every dollar withdrawn from a pre-tax 401(k), IRA, pension or cash balance plan is taxed as ordinary income in the year it comes out, at federal and state rates. How much you pay depends on when and how fast you take it: the same $2.5 million balance can cost more than $850,000 or around $210,000 in federal tax depending on the exit. See your own spread.

What is the federal estate tax exemption in 2026?

The federal estate tax basic exclusion is $15,000,000 per person for deaths in 2026, or $30,000,000 for a married couple using portability, per the IRS. Estates above it are taxed at up to 40%. Check your exposure.

What are the 2026 federal income tax brackets for married couples?

For 2026, married couples filing jointly pay 10% up to $24,800 of taxable income, 12% to $100,800, 22% to $211,400, 24% to $403,550, 32% to $512,450, 35% to $768,700 and 37% above that, after a $32,200 standard deduction (IRS Rev. Proc. 2025-32).

Why do high earners in California pay so much tax?

High earners in California stack the 37% top federal rate on top of a state rate that reaches 12.3%, plus a 1% Mental Health Services Tax on income over $1 million. Wages also carry Medicare and the 0.9% Additional Medicare Tax, and investment income can add the 3.8% Net Investment Income Tax.

Strategies

What is a cash balance plan?

A cash balance plan is a type of defined benefit pension that lets a business owner contribute far more pre-tax than a 401(k) allows, often $100,000 to $300,000+ a year depending on age and income. How cash balance plans work.

What is premium financed life insurance?

Premium finance means a lender pays most of the premiums on a large permanent life insurance policy while your own capital stays invested. It is built for high-net-worth, accredited investors and carries loan-rate and policy-performance risk that must be stress-tested. How premium finance works.

What is the difference between IUL and PPLI?

Indexed universal life (IUL) credits interest linked to a market index with a floor, and is available to most healthy buyers. Private placement life insurance (PPLI) holds investment accounts inside a policy and is limited to accredited investors and qualified purchasers. Both can grow and pay out tax-free when structured correctly. Compare IUL and PPLI.

How does a charitable LLC help with capital gains?

A charitable LLC is used here for capital gains and estate planning, giving you control over how and when appreciated assets are used for charitable goals. Tyler does not use it as an income-tax deduction play. How the charitable LLC fits.

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