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Nobody sits you down and teaches you how to vet a financial advisor. You learn to read a defense, break down film, and train your body for a job most people never see up close. Nobody trains you to sit across from someone asking for your trust and your money. That gap is where a lot of athletes get burned. Not because they made a bad decision on purpose, but because nobody ever showed them what a good decision looks like in that specific chair.

This isn't a generic checklist copied from a personal finance blog. It's built around what you're actually dealing with. Below are the 9 questions worth asking before you hand anyone your trust, plus a few signs it's time to walk away. Our own answers are at the bottom, because we think you should hold every advisor you talk to, including us, to the same standard.

1. Are you always a fiduciary?

A fiduciary is legally required to act in your best interest. Some advisors only wear that hat part of the time, depending on which license they are using for a given recommendation. Ask them to put it in writing.

2. How do you get paid?

Fee-only means every dollar comes from you, the client. AUM percentage, flat fee, or a mix of the two. Commission and fee-based models create a conflict of interest by design, since the advisor gets paid more for selling certain products whether or not those products are actually best for you.

3. Have you worked with athletes before?

Athlete income does not look like normal income. NIL deals, signing bonuses, escalators, guaranteed money versus non-guaranteed, short career windows, sudden retirement risk. An advisor who has never planned around this is learning on your dime.

4. What's your plan for loss-of-value or disability insurance?

Your body is the asset. An advisor who has never brought up loss-of-value or disability coverage has not thought seriously about how you actually make money.

5. How do you plan around taxes?

Investment returns get all the attention, but taxes quietly take more of your money than any bad investment ever will. NIL income especially catches athletes off guard, since it often comes in as self-employment income with nothing withheld.

6. How do you work with my family and other advisors?

You need a CPA, an attorney, and an advisor working together, not in silos. Your family needs to be part of that conversation too, especially once NIL contracts, collectives, or agents are in the picture.

7. What is your investment philosophy?

If an advisor cannot explain their approach without jargon, that is a problem. You should walk away understanding why they invest the way they do, not just trusting that they do.

8. What does "high touch" actually mean?

Some advisors take on hundreds of clients and call it a relationship. Ask how many households they serve and what your actual access looks like.

9. What if I get traded or relocate?

That includes the transfer portal, not just a trade. Life moves fast in this business, and your plan needs to move with it.

3 red flags to walk away from

Even after you narrow the list down, watch for these:

1. They cannot clearly explain how they get paid.
2. They use fear tactics to rush your decision.
3. All they pitch is products or investments, never a plan.

If you see any of these, keep looking. It is not worth the risk.

The bottom line

Your choice of a financial advisor is one of the most important decisions you will make in your career. This team will be with you before, during, and after your playing days, and they are tasked with making sure you maximize every dollar you earn. A money mistake for a professional athlete is not a small setback. The impact is wide-ranging, and there is rarely a second chance.

Ask these 9 questions. Write down the answers. Compare them across every advisor you talk to.

FAQ: How we answer these at WIN Private Wealth

Are you always a fiduciary? Yes, always. WIN Private Wealth is an independent, fee-only fiduciary RIA. Every recommendation we make, on every account, is held to that standard. We will put it in writing.

How do you get paid? We are fee-only. AUM percentage, flat fee, or a mix of the two depending on where you are in your career. No commissions, no product sales, no kickbacks from an insurance company or fund company sitting behind the curtain. Every dollar we make comes from our clients and nowhere else.

Have you worked with athletes before? This is our focus, not a side practice. Our athlete division is led by a Fresno State and NFL veteran who has lived the exact transition our clients are navigating, from locker room to boardroom. We build every plan around rookie contracts, NIL cash flow, and the CBA specifically because generic financial planning does not fit an athlete's timeline.

What's your plan for loss-of-value or disability insurance? We walk through coverage options as part of onboarding, not as an afterthought brought up after something goes wrong. Protecting the asset that generates your income is part of the plan from day one.

How do you plan around taxes? Taxes are core to what we do, not an add-on. We coordinate directly with your CPA on entity structure, state residency, and how NIL and signing bonus income should be timed and structured. We have built our own NIL tax planning tools specifically because we got tired of seeing athletes blindsided every April.

How do you work with my family and other advisors? We build a full team around you, including your CPA, attorney, and agent, and we make sure everyone is working from the same plan instead of three different ones. We also make time to talk directly with the family members involved in your finances, because clear communication early prevents bigger problems later.

What is your investment philosophy? We build around three principles: protect what you have already earned, produce steady infrastructure and income, and pursue long-term growth once that foundation is solid. We can walk you through exactly why your portfolio is built the way it is, in plain language, every time you ask.

What does "high touch" actually mean? For us, it means a defined client group, not hundreds of households split across a call center. You get direct access to your advisor, not just an assistant, and proactive check-ins instead of waiting for you to reach out first.

What if I get traded or relocate? We build around tax changes, contract logistics, and the cost of a sudden move into your plan before they happen, not after. When your situation changes, your plan adjusts with you, and we are the ones who bring it to you rather than waiting for a phone call.

If you are a professional or college athlete earning NIL and you are looking for a financial team built around you, schedule a call and talk with an advisor.