Tax Strategy For High Earners
Play The Long Game With Your Money.
Tax strategy and advanced life insurance planning for business owners, athletes, physicians and executives earning $500K or more. Tyler starts with your tax bill, today's and the one waiting in your retirement accounts, and works alongside your CPA.
The 19th hole isn't the end of the game. It's where the real strategy happens.
- Turned Pro 2012
- PGA Tour Canada 2014 & 2016
- 8 Years Of Professional Golf
- Works Alongside Your CPA
The Second Bill
Every Tax Bill Has A Score.
The Second Bill is the income tax due when money comes out of a pension, cash balance plan or pre-tax 401(k). You deducted it going in. How it comes out decides how big the second bill is.
Illustrative example, not a projection for any client. Balance is the median employer's plan assets across public DOL Form 5500 filings. Federal income tax only, 2026 married-filing-jointly brackets, no growth, no state tax. Your numbers will differ.
The Approach
Save The Tax First. Then Put It To Work.
Most advisors open with a product. Tyler opens with your tax bill. The plan starts by finding the dollars you are overpaying today, then moves those savings into structures that grow and pay out tax-free.
- 1Find the leak. Three numbers side by side: this year's tax bill, the tax waiting in your retirement accounts, and your estate exposure.
- 2Cut it. Qualified plans such as cash balance plans, the timing of income and exits, and advanced tax strategies, reviewed with your CPA before anything is filed.
- 3Redeploy it. Part of what you save funds structures that grow tax-deferred, can be accessed tax-free and protect your family.
Who's In The Field
Once income passes $500K a year, the rules of tax planning change. Tyler works where they change.
Business Owners
Cash balance and defined benefit plans can shelter $100K to $300K+ a year. Then there is the tax on the way out.
Business Owner Planning →Athletes
Peak earning years are short and taxed at the top. The plan turns a short window into lasting, tax-advantaged wealth.
Athlete Planning →Physicians
Top federal and California brackets on every extra shift. Practice owners have more levers than they are using.
Physician Planning →Executives
RSUs, bonuses and liquidity events land in one tax year. The plan is built around those moments before they happen.
Executive Planning →
Works With Your Team
You Make The Calls. Tyler Carries The Bag.
A great caddy reads the course, hands over the right club and keeps the round moving. Tyler does the same for your money, while your CPA, attorney and advisors keep their seats. Every decision stays yours.
- Reads The CourseBuilds your Tax Advantage Scorecard and the game plan.
- Picks The ClubDesigns the insurance and matches each strategy to your numbers.
- Briefs Your TeamWalks your CPA and attorney through every move before anything is filed or signed.
- Keeps The PaceRuns the timeline so nothing stalls between meetings.
Your Team Keeps Their Seats
- Your CPAReviews every strategy and files the return.
- Your AttorneyDrafts or reviews trusts, entities and agreements.
- Business ManagerRuns cash flow and bill pay.
- Your AdvisorsWealth manager, banker, anyone else you trust.
Your Round, Hole By Hole
What happens after you book: five meetings, each with a clear outcome. You decide at every hole whether to keep playing.
- Hole 1
Pre-Round Discovery
Discovery Meeting
A 30-minute conversation about your income, goals and what you already have.
You leave with a straight answer on whether advanced planning fits.
- Hole 2
Course Assessment
Assessment Meeting
We review what you share, such as returns, plan statements and policies, and fill the gaps.
You leave with a complete picture of where your tax is going.
- Hole 3
The Turn
Tax Advantage Scorecard & Game Plan
Your numbers side by side, and the specific plan that brings them down.
You leave with your Scorecard and a written game plan.
- Hole 4
Back Nine
Game Plan Activation
Plan setup, applications and coordination with your CPA and attorney.
You leave with every piece in motion, on a timeline.
- Hole 5
19th Hole
Onboarding & Ongoing Optimization
Onboarding once approved, then regular reviews as your income, the tax code and your goals change.
You leave with a plan that keeps up with you.
Run The Numbers Before You Call
Three free calculators built on 2026 federal brackets. No email required.
Calculator
Your Tax Scorecard
Today's tax bill, your pile at retirement and what it costs in tax to live on it.
Open The Scorecard →Calculator
The Second Bill
The federal tax on your pension or cash balance plan under four different exits.
See Your Spread →Calculator
Estate Tax Exposure
What your heirs owe under the 2026 $15M exemption, today and as your net worth grows.
Check Your Exposure →
Your Strategist
A Former Pro Reads Your Course
Tyler Ostrovsky was an All-Patriot League golfer at Lafayette College, turned professional in 2012 and played eight years of pro golf, including status on PGA Tour Canada. Today he builds tax strategy and advanced life insurance plans for people whose earning windows look a lot like an athlete's: big, and shorter than they think.
From The Course To 19th Hole
- 2008 Lafayette College
- 2012 Turns Professional
- 2014 PGA Tour Canada
- 2021 True Path Financial
- 2024 Diamond Club
- Now 19th Hole Financial
“The 19th hole isn't the end of the game. It's where the real strategy happens. Same principle applies to your wealth.”
From The Library
Plain-English guides, sourced to the IRS and the tax code. All Insights
Questions
Straight Answers
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.
Play A Round With Tyler.
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