The Silent Signs You've Outgrown Your Wealth Advisor as a Professional Athlete
- Brendan Fraleigh
- 3 days ago
- 7 min read
I have spent years sitting across the table from athletes and their families.
From 1st round draft picks, to league all-stars, to guys who've earned $100M+ in their careers.
Here's the thing I have noticed working with players at your stage of your career. Nobody ever benches their wealth advisor. You'll change agents. You'll change trainers. You'll change your diet, your workout program, anything that stops working the way it used to.
But the guy managing your money?
For most players, that's the one relationship that never gets a second look, no matter how much has changed since it started.
In today's blog, I want to walk through why that happens, and the silent signs that tell you it might be time for a real conversation with your wealth advisor as a professional athlete.
Why This Relationship Never Gets Re-Evaluated
Every other relationship in your career has a built-in trigger to reassess it.
A bad season. A poorly negotiated contract. A trainer who can't get you healthy. Something breaks, and you notice.
The relationship with your wealth advisor doesn't work that way.
There's no bad game to point to. No box score. Just statements that show up, a call once or twice a year, and the assumption that if nothing feels obviously wrong, everything must be fine.
That's the trap.
Because "nothing feels obviously wrong" and "this is actually working as well as it could be" are two completely different things, and most players have never had a reason to find out which one is true.
The Advisor Who Got You Here Was Solving a Different Problem
Think about who you hired, and when.
For most players, that relationship started early.
Maybe it was someone your agent recommended. Maybe it was someone your family knew. Maybe it was whoever showed up at the right moment when you were 21 and needed someone, anyone, to help you figure out what to do with your first real contract.
That person was solving a 21-year-old's problem.
First contract
First real money
Basic questions
Get the fundamentals in place
But you're not that guy anymore.
Your contracts have gotten bigger.
Your questions have gotten more complicated. Here's the reality:
You are closer to retirement than you are to your first year in The Bigs.
You're at the point now where you need to start thinking seriously about what life looks like after the game ends. That can be a daunting reality to face.
So the question worth asking isn't whether your advisor was good at the job in year one.
It's whether the relationship has actually grown alongside everything else in your career, or whether you're still getting the same conversation you were getting back then, just with bigger numbers attached to it.
The Silent Signs
It's at this point where I want to share with you some of the silent signs I have seen as a wealth advisor for professional athletes that oftentimes go missed. Here's what I'd actually pay attention to:
You couldn't explain your own plan if someone asked you to.
I am not talking about the balance in your investment account. I am talking about the plan.
What happens after I hang it up?
Where will my money come from?
What happens if I am not here in 5 years?
What if I want to start a second career? Does my plan include that option?
These are all questions that are different from when you first started.
And questions that, quite frankly, should have been answered years ago.
Every conversation feels the same, no matter how much has changed.
This one doesn't get talked about enough. Guys, if your advisor is showing you the same "summary" of your investment performance, something is not right. Your advisor needs to be reviewing everything with a dollar sign in front of it. Your cash flow. Your tax plan, Your estate plan. Your insurance coverages. These things need to be reviewed yearly (at the very least).
It is the little things that set your advisor apart, especially as you near this new stage of life.
You've never been asked a real question about your career, only talked about money.
You are going to be a retiree a lot longer than you will be a professional athlete.
And with that comes new realities.
Have you talked to your advisor about:
How much longer you realistically plan to play
What happens if it your career ends earlier than expected
Can I sustain my lifestyle without a constant paycheck
All of these questions are honest and realistic, but have very little to do with "investments."
You find out about big financial moves after they've already happened.
I hear it over and over again from guys we have brought on after they have been with an advisor. "Well, he came in with a fancy suit, threw a bunch of terms at me I've never heard of, but said I was all good." Let me tell you something, this is not healthy. You don't need to be the financial expert. But you should be able to understand your financial plan and why it is being recommended. If that's not the case, it may be time to get another opinion.
You've never once heard "I don't think that's the right move for you."
I am all about building true, authentic relationships. But with that, comes someone who is not afraid to tell you no. If you think about all the important people in your life. The people who you trust with every ounce of strength you have. I'd bet they would be someone who isn't afraid to tell you the truth. When it comes to managing your money, if your advisor is a "yes man" then they are more interested in keeping you comfortable than looking out for your best interest.
Nobody has ever proactively brought up post-career planning.
When we first start working with guys, this is a topic of conversation.
It's almost like we are working backwards.
Father time is undefeated. Professional sports will end.
And when it does, what do you want it to look like?
If you've been in the league for years and nobody's asked what you actually want your life to look like when this ends, they aren't looking at protecting your financial future.
Loyalty Isn't the Same as Fit
Here's what stops most players from ever looking into this.
It feels disloyal.
This is the guy who was there from the beginning.
Bringing in a second opinion feels like a betrayal of that, so guys just don't do it, even when something feels a little off.
I understand that instinct.
But loyalty to a person and fit for where you are in your career are two different things, and confusing them is exactly what keeps players stuck with a setup that stopped serving them years ago.
A second opinion isn't a betrayal.
It's due diligence, the same kind you'd expect from any other part of your professional life.
Nobody thinks twice about getting a second opinion on a medical decision, a contract negotiation, or a major business move.
Your entire financial future deserves at least that same level of scrutiny, especially at this stage of your career.
What a Real Second Opinion Actually Looks Like
No good advisor is in the business of taking you away from good relationships.
Well, at least they shouldn't be. However, a great advisor asks a few honest questions to see how the answers land.
Can your current advisor clearly explain what your plan is actually built around?
Do they understand your specific career, your specific league's structure, and what your timeline realistically looks like?
Have they ever told you no?
Do they know what you actually want your life to look like after this career ends?
If those answers come easily and confidently, that's a good sign.
If they don't, or if you realize you've never actually asked, that's worth sitting with.
Final Thought
The players who come out of professional sports in the strongest position aren't always the ones who made the most money.
They're the ones who never let a relationship coast just because it was comfortable, especially the one responsible for their financial life.
You wouldn't run the same training program you had at 21.
You wouldn't take advice from a coach who stopped adjusting to who you've become.
Your financial plan deserves the same standard.
If it's been awhile since you've actually stress-tested that relationship, I would start now.
If you are at this point in your career and want a second opinion, schedule a call with a Moment Founder.
Not sure what questions to ask, check out this video on 10 questions you should ask when interviewing a financial advisor.
Get in Touch With An Advisor
Frequently Asked Questions
Here are some answers to questions I receive frequently from professional athletes.
How do I know if it's time to get a second opinion on my financial advisor?
If you can't clearly explain your own plan, if every conversation feels the same regardless of what's changed in your career, or if post-career planning has never come up, those are all signs worth paying attention to.
Isn't switching financial advisors disruptive?
Not when it's done right. A good second opinion starts with a conversation. You are simply gathering information, not blowing anything up.
How is Moment Private Wealth different from a typical financial advisor?
We work specifically with athletes and business owners, which means we understand career structures, contract timing, and post-career planning in a way a generalist advisor typically doesn't. We also have the fire power to deliver for you as a professional athlete.
What does your average client look like?
Our clients are nearly all athletes and business owners. Our average client has a net worth greater than $5M. The strategies, solutions, and planning that we implement have a high-net-worth and ultra-high-net-worth client in mind.
Why should I consider hiring Moment Private Wealth?
Great question! But first, let us explain why you shouldn’t hire us. If you’re looking for an advisor who will pitch shiny object investments or be a “yes man” you are in the wrong place. Why? Because we believe in being truth tellers and only giving advice that we take ourselves. The investments, strategies, and planning we do are all things our advisors do with their own money. If you are an athlete or business owner interested in things like lowering your tax bill, investing smarter, and finding a trusted partner we might be a good fit.
*Moment Private Wealth offers information on tax and estate planning that is general in nature. Tax and Legal advice are not provided by Moment Private Wealth. Consult an attorney or tax professional regarding your specific legal or tax situation.
Comments