Tax Strategy for Athletes & High Earners

You Have an Agent, a Financial Advisor, and a CPA. Family Offices Have a Fourth Person — Do You?

I got off the phone recently with J.R. Tolver — former NFL wide receiver for the Dolphins, Panthers, and Cowboys, and now CEO of Athlete Mogul, where he coaches athletes on building life and business beyond the game. We got to talking about the team every athlete and high earner assembles around their money: the agent who negotiates the deal, the financial advisor who invests it, and the CPA who files the return every April.

Three people. Three functions. And most people stop there — because most people don’t know there’s a fourth seat at the table, and that leaving it empty is quietly costing them more than any of the other three will ever save them.

Family offices don’t run on three advisors. They run on a full team built specifically to keep more of what’s earned — and at the center of that team is a tax strategist. It’s not a luxury reserved for nine-figure net worths. It’s a role. And if no one is sitting in it, you’re the one absorbing the cost.

The Three Everyone Already Has

Look at any athlete’s or executive’s advisory team and the same three roles show up:

→ The agent negotiates contracts, endorsements, and deals.

→ The financial advisor takes what’s earned and puts it to work — investments, retirement, long-term growth.

→ The CPA reports what happened last year and files the return on time.

Every one of those roles is necessary. None of them is designed to do what a tax strategist does. That’s not a knock on any of them — it’s just not their job.

The Difference Between a CPA and a Tax Strategist

A CPA is built for compliance. They look at what already happened — the income you earned, the deals you closed, the year that’s already over — and they file it accurately and on time. That’s essential. It’s also, by definition, reactive.

A tax strategist is built for what happens before the year closes. Entity structure. Timing of income. Retirement and deferral vehicles built around a signing bonus or an endorsement payout. Real estate and depreciation strategy. Multi-year planning that lines up with a career that might peak for five or ten years and then look completely different. That work has to happen while there’s still time to act on it — not in March when the prior year is already locked.

The Simple Version

A CPA tells you what you owe. A tax strategist works to make sure you never owed that much to begin with.

Why Athletes and High Earners Feel This the Most

This gap matters for anyone with real income, but it hits athletes, entertainers, and content creators the hardest, for a simple reason: the shape of the income is unusual. A signing bonus, a shortened earning window, endorsement income on top of a W-2, appearance fees, licensing — none of that fits neatly into a standard withholding table, and none of it gets fixed after the fact. Without someone whose full job is to plan around that shape in advance, the standard withholding and standard deductions do the planning for you. That’s rarely the outcome anyone would choose on purpose.

Without that fourth seat filled, here’s what tends to happen:

→ Entity structure gets set once, early, and never revisited as income grows.

→ Big payouts hit in a single tax year with no strategy to spread or shelter them.

→ Retirement and legacy planning happen through generic products instead of a plan built around the actual career timeline.

→ Nobody catches it, because the agent isn’t looking at taxes, the financial advisor isn’t looking at entity structure, and the CPA isn’t looking at next year until it’s already this year.

The Fourth Seat

That conversation with J.R. is the reason I’m writing this. It’s the same thing I tell every athlete, entertainer, and high-income earner I sit down with: the team you build early determines how much of what you earn you actually get to keep. Family offices figured this out a long time ago — a tax strategist isn’t an add-on, it’s a standing seat at the table, working year-round alongside the agent, the advisor, and the CPA instead of after them.

You don’t need a family office budget to have that seat filled. You need someone whose only job is to look ahead at what you’re earning and build the structure around it before the year closes — not report on it after.

Is your fourth seat filled?

If you don’t have a tax strategist working proactively alongside your agent, advisor, and CPA, let’s talk about what that seat should look like for you.

Book Your Consultation

Jarret Willey is the founder of JW Tax & Consulting, LLC, a veteran-owned tax strategy firm serving business owners, professional athletes, entertainers, and high-income earners nationally. Learn more at jwtaxandconsulting.com/athletes-and-entertainers.