Chapter One
The Golf Years
Tyler grew up in Simi Valley, California, and played for Simi Valley High School before heading east to Lafayette College in Pennsylvania. As a Lafayette freshman he finished tied for seventh at the Patriot League Championship and made the All-Patriot League second team. He was named First Team All-Patriot League as a sophomore after a third-place finish at the conference championship, and second team again as a junior.
He turned professional in 2012 and played for eight years. The high point was PGA Tour Canada, where he held full status in 2014 and partial status in 2016. Much of the rest was mini-tour golf: unaffiliated events where players pay their own entry fees and get paid only when they finish high enough.
Chapter Two
Why Golf Explains The Planning
A tour player learns early that a career can be long or short, and the paychecks arrive unevenly. Most high earners face the same shape: a doctor's peak years, a founder's liquidity event, an athlete's contract, an executive's vesting schedule. The money arrives in large, uneven pieces, taxed at the top rate on the way in and again on the way out.
- Read The Whole Course First.Every plan starts with three numbers side by side: this year's tax, the tax waiting in your retirement accounts, and your estate exposure.
- Play The Shot In Front Of You.Five meetings, one clear outcome each. You decide at every hole whether to keep playing.
- Know When To Press And When To Protect.Some years call for aggressive deferral. Others call for locking in what you have. The plan says which, and why.
- Adjust To The Conditions.Income, the tax code and your goals move. Regular reviews keep the plan current with all three.
- Nobody Plays It Alone.A tour player has a coach and a caddie. Your plan has your CPA, your attorney and Tyler, each in their own seat.
Chapter Three
The Practice Today
Tyler joined True Path Financial Partners in March 2021 and qualified for President's Club, then Diamond Club in 2024. He founded 19th Hole Financial to focus on high earners where tax planning and advanced life insurance meet: cash balance and defined benefit plans for business owners, premium finance, indexed and private placement life insurance, charitable LLC planning for capital gains and estates, and retirement tax planning.
His approach in one line: save the tax first, then put the savings into a structure that grows and pays out tax-free. He works alongside your CPA and attorney, and they review every strategy before anything is filed or signed.
The Card
Credentials And Records
- Professional golfTurned pro 2012 · PGA Tour Canada: full status 2014, partial status 2016 · PGA Tour profile
- College golfLafayette College · First Team All-Patriot League 2008–09 · Second Team 2008 and 2009–10 · Lafayette roster
- RecognitionPresident's Club · Diamond Club 2024
- HometownSimi Valley, California
- LicenseCalifornia insurance agent, License #4102745
- FirmTrue Path Financial Partners since March 2021 · Firm profile
Most of Tyler's clients arrive through someone they trust. If a friend, colleague or client comes to mind, the referral page takes two minutes and asks for no financial details. CPAs, attorneys and advisors can use the professional introduction page.
The 19th hole isn't the end of the game. It's where the real strategy happens. Same principle applies to your wealth.
Tyler Ostrovsky · Founder, 19th Hole Financial
