Nov 13, 2025 Winning Beyond the Game: A Playbook for Lifelong Financial Success

In professional sports, the spotlight shines brightly, but the earning years can be fleeting. Many athletes see sudden wealth at a young age—sometimes even before they’re legally old enough to toast a contract signing. Without the right strategy, that wealth can disappear just as quickly as it arrives.

Brock Wilson, President of the Sports & Entertainment Team at TSG Wealth Management, has spent his career helping athletes build the structures and habits that turn short earning windows into lifelong prosperity. He shares insight on the practical steps athletes should take to secure their financial futures.

Can you share your background and why you focus on athletes and entertainers?

I’ve been in wealth management for over two decades, and during that time I’ve seen the incredible opportunities—and challenges—that professional athletes face. Many of them achieve a level of financial success at a young age that most people don’t see in a lifetime. But with that comes pressure, complexity, and the responsibility of managing wealth for not just themselves, but potentially their families and future generations.

At TSG Wealth Management, I lead our Sports & Entertainment team, and our mission is to give these clients the tools, education, and support they need to build lasting legacies. Helping an athlete create a strategy that allows them to live well today and still be secure for decades to come — that’s the work I’m passionate about.

What’s the biggest mistake you see young athletes make with their money?

The number one issue is not planning early enough. When you sign your first contract, it feels like the money will never stop coming. But careers can be short, unpredictable, or even end overnight due to injury. If you don’t set the foundation right away, you may not get another chance.

We teach our clients to think of their career earnings as the seed of a business. If you treat a $20 million contract like $20 million in spending money, it will disappear. If you treat it as the foundation of a financial enterprise, it can support you—and your family—for the rest of your life.

So what does that foundation look like in practical terms?

First, it’s about creating structure. We start with basics like mandatory tax withholdings, automatic savings, and a budget that ensures lifestyle choices are sustainable. Then we focus on long-term investment vehicles—things like diversified portfolios, retirement accounts, real estate and in some cases, private investments that fit the client’s goals.

Another big piece is insurance and risk management. Athletes have unique risks—career-ending injuries, short contract durations, or endorsement deals that can disappear quickly. Providing income streams and creating safety nets is critical.

Finally, we work to build an estate plan strategy from the beginning. Even if you’re 18 years old, you need to think about preserving wealth, avoiding unnecessary taxes, and setting up a framework for your future family.

How important is education in the process?

Education is everything. Without it, even the best wealth plan won’t stick. From day one, we make education a priority. That means timely calls to review strategies, answer questions, and keep clients engaged with their own financial picture.

We also run webinar series and workshops specifically designed for athletes and their families, covering everything from basic budgeting to advanced investment concepts. The goal is to demystify finance and make sure clients understand why certain strategies are in place—not just what they are.

And we don’t wait until the first paycheck to start. If a young athlete or their family comes to us before the money even arrives, that’s the best time to begin. Starting early allows us to build financial literacy before big decisions need to be made. When athletes truly understand how their money works, they’re much more likely to stick to the plan and avoid costly mistakes.

How important is it for an athlete to have a team of advisors rather than just one person?

It’s absolutely essential. No single advisor can do it all. You need a coordinated team that includes a wealth manager, CPA, attorney, insurance specialist, and sometimes even business managers who understand brand deals and endorsements.

What makes TSG unique is that we serve as the quarterback. We bring all of those professionals together under one cohesive strategy so the athlete isn’t stuck trying to manage a dozen moving parts. That coordination is what prevents mistakes and makes sure opportunities aren’t missed.

NIL money has changed the game, with athletes earning earlier than ever. What’s your advice for a 19-year-old signing their first endorsement?

Start with education. We spend a lot of time teaching young athletes—and their families—about how money works. A $500,000 check is not $500,000 of spending money. Taxes, savings, and long-term goals all come first.

We often host family education sessions because the support system around the athlete needs to be aligned. When everyone understands the plan and the purpose, it’s much easier for the athlete to stick to it. The earlier those habits are formed, the more powerful compounding and disciplined investing become.

What should athletes be looking for when choosing a wealth manager?

Three things: experience, transparency, and fit. Experience matters because athletes face unique challenges that not every advisor understands. Transparency is key—you should know exactly how your advisor is compensated and what their strategy is. And fit is about trust and communication. If you don’t feel comfortable picking up the phone to call your advisor at any time, it’s not the right fit.

At TSG, we see ourselves as part of the athlete’s inner circle. We don’t just manage investments; we manage risk, educate, and help clients build a sustainable future.

If you could leave young athletes with one message about financial success, what would it be?

Don’t think in seasons—think in decades. Your playing career is temporary, but your life is long. The choices you make with your first contract can set you up for life or set you up for stress.
With the help of the right strategy, discipline, and support team, it’s possible to turn peak career earnings into lifelong security and even multigenerational wealth. That’s what we aim to do every day at TSG, and it’s what I love most about this work—helping athletes win not just in the game, but long after it’s over.

Final thoughts—why should someone in sports trust TSG’s Sports & Entertainment team?

Athletes only get one shot at turning peak earning years into lifelong financial stability. That’s why partnering with the right wealth management team matters. At TSG Wealth Management, Brock Wilson and the Sports & Entertainment Team help provide the structure, education, and long-term strategy athletes need to thrive long after the spotlight fades.

For more information, visit the Sports & Entertainment page or explore the full TSG Wealth Management site at TSGWM.com.

Investment products and services are offered through Wells Fargo Advisors Financial Network, LLC (WFAFN), Member SIPC. TSG Wealth Management is a separate entity from WFAFN.