Jul 20, 2026 Investing Like It Has to Last: How Athletes Should Think About Building Long-Term Wealth

For most people, wealth accumulates gradually over decades. For professional athletes, it arrives fast, peaks early, and then stops — often before age 35. In this Q&A, Joshua Turley, Managing Director at TSG Wealth Management and Co-Founder of TSG’s Sports & Entertainment Team, draws on more than 20 years of experience and his dual CFP® and CFA® designations to discuss what a client-first investment approach looks like for athletes. From compressed earning timelines and irregular income to the emotional pressures that surround financial decisions in the sports world, Josh explains why rigorous analysis and long-term discipline are the foundation of lasting wealth — and why the time to build it is always right now.

Josh, you hold both the CFP® and CFA® designations — which is relatively uncommon. How does that shape the way you approach investment planning for athletes?

The CFP® designation is about the full picture — life planning, cash flow, insurance, estate planning strategies, retirement readiness. The CFA® is deeply analytical, focused on investment theory, portfolio construction, and understanding how markets actually work. Most advisors have one or the other. Having both means I can sit with an athlete and connect the human side of their financial life directly to the investment decisions that should be supporting it.

In sports, that combination matters almost more than anywhere else. The stakes are high, the timelines are compressed, and the margin for error is small. When I’m building an investment strategy for an athlete, I’m not just looking at returns in isolation — I’m looking at how the portfolio integrates with their contract structure, their tax obligations, their lifestyle needs, and the future they’re trying to build. That requires both sets of skills working together.

How is investment planning fundamentally different for a professional athlete compared to a traditional high-net-worth client?

The math is different. A corporate executive might spend 35 years accumulating wealth at a relatively steady pace. An athlete may earn the equivalent in 5 to 10 years — and then stop. That compression changes everything about how you approach the strategy.

When you have decades to accumulate wealth, you have time to recover from mistakes. If a bad investment costs you two years of growth, you have 30 more years ahead of you. An athlete doesn’t have that buffer. Every major financial decision carries more consequence, which means the analytical rigor behind the strategy has to match the stakes. We can’t afford to learn on the job with an athlete’s money. We have to get it right from the beginning — and then stay disciplined regardless of what pressure or opportunity shows up along the way.

What does a sound investment foundation actually look like for an athlete early in their career?

It starts with liquidity. Before anything else, an athlete needs accessible cash reserves that can sustain their lifestyle and obligations if income stops suddenly — which it can, at any time. A career-ending injury doesn’t come with a warning. That liquidity layer is the first thing we establish, and it’s non-negotiable.

From there, the focus shifts to building a diversified long-term investment portfolio across multiple asset classes: equities, fixed income, real assets including real estate, and in some cases, carefully vetted alternative investments. The goal is to build wealth that grows independently of the athlete’s career, so that when the career ends, the portfolio is already capable of carrying the financial load. That transition shouldn’t feel like a cliff. If the planning is done right, the athlete’s financial life continues on a sustainable trajectory long after the final game.

Large, irregular payments — signing bonuses, roster bonuses, endorsement deals — are a constant feature of athlete finances. How should those be handled?

With a plan in place before the money arrives, not after.

The most common mistake we see is treating a large payment as income available to spend. It isn’t — at least not in full. A meaningful portion has to be set aside immediately for taxes. The “jock tax” alone, which requires athletes to file returns in every state where they play or earn, can represent a significant liability that catches athletes off guard if they haven’t planned for it. Beyond taxes, the remainder should flow into a structured investment plan based on the athlete’s long-term goals, not into lifestyle expansion or opportunistic investments that haven’t been properly vetted.

We coach our clients to treat those large payments as foundational capital. They’re not a windfall — they’re the building blocks of a financial life that has to last 40 or 50 years. The discipline to treat them that way is one of the most important habits we work to establish early in the relationship.

You mentioned vetting investments. That’s a significant issue in the sports world. How do you handle the constant stream of investment opportunities that athletes receive?

We take every request off the athlete’s plate entirely and run it through a structured review process. That means looking at the fundamentals — the business model, the principals involved, the financial projections, the liquidity terms — before we ever bring it back to the client for a conversation.

The reality is that most of what comes through doesn’t survive basic scrutiny. That’s not because the people bringing ideas are bad actors, though that does happen. It’s because a lot of what gets pitched to athletes is speculative, illiquid, poorly structured, or simply outside the risk parameters that match their overall plan. Our job is to be the filter — so the athlete can say, “Talk to my team,” and trust that anything that comes back to them has already been evaluated honestly.

The emotional side of this matters, too. Athletes are often approached by teammates, family members, former coaches, and close friends. The social pressure to say yes — to support someone they care about, or to be seen as successful off the field — can override good judgment. Having a process in place gives athletes a rational framework to fall back on, and it gives them a way to decline gracefully without damaging the relationship.

How does the TSG Sports & Entertainment team’s client-first approach shape the investment strategy you build for athletes?

It means the strategy starts with the client, not with a product or a model portfolio. Before we make a single investment recommendation, we spend real time understanding who the athlete is, what they want their life to look like, what they’re afraid of, and what success means to them on their terms.

That foundation changes everything about what comes next. Two athletes with identical contract values might need completely different investment strategies based on their family situations, their post-career goals, their risk tolerance, and their timelines. A client-first approach means we never assume — we ask, we listen, and we build accordingly.

It also means we stay connected throughout the relationship, not just at onboarding. Circumstances change. Contracts get restructured. Careers end earlier than expected. A client-first practice adapts to the client’s reality as it evolves, rather than fitting the client into a strategy that no longer fits their life.

What’s the most common investment mistake you see athletes make, and how do you help them avoid it?

Concentrating too much wealth in a single asset or a single bet. It shows up in different forms — sometimes it’s real estate, where an athlete has poured a disproportionate share of their net worth into property. Sometimes it’s a business venture. Sometimes it’s a single stock or a private equity position that was pitched as a sure thing. Concentration feels like conviction, but in investing it’s almost always just risk that hasn’t shown itself yet.

Diversification sounds basic, but it’s genuinely one of the most powerful tools available — and one of the hardest to maintain when someone is excited about an opportunity or confident in their own judgment. We spend a significant amount of time educating clients about why the portfolio is structured the way it is, so that when the pressure to deviate comes — and it always comes — they understand what they’re protecting and why the structure matters.

How does investment planning connect to the post-career transition you work through with athletes?

They’re inseparable. The investment decisions made during the playing years are what determine what post-career life actually looks like. If the wealth was built thoughtfully — diversified, growing, structured to generate income — the transition can be a genuine next chapter. If it wasn’t, the transition becomes a financial crisis dressed up as retirement.

We start the post-career conversation from the first meeting, not the last one. What does the athlete want that chapter to look like? Do they want to stay involved in sports? Build businesses? Travel? Provide for their family for generations? Whatever the answer, the investment strategy during the playing years has to be designed with that destination in mind. The career is the runway. The portfolio is what carries them after liftoff.

Whether you’re a sports attorney or an agent, you’re often the most trusted voice in an athlete’s corner. How can those professionals better support their clients’ long-term financial outcomes?

Ask the question earlier than feels necessary. Attorneys are focused, understandably, on the legal work in front of them — the contract, the negotiation, the deal. Agents are focused on the relationship and the next opportunity. But the financial reality that those decisions create is something athletes often don’t fully understand until years later. Whether you’re structuring a contract or negotiating an endorsement, asking “Do you have a wealth management team in place, and are they involved in how we’re approaching this?” is serving the client in a way that goes beyond the immediate transaction.

We’ve found that the most successful client outcomes come when legal, representation, and financial advisors are genuinely aligned — each understanding how their piece of the picture connects to the others’. That coordination doesn’t require extra work from the attorney or the agent. It just requires the introduction. And that introduction, made at the right moment, can be one of the most consequential things either professional does for an athlete’s long-term security.

Final thought — what do you most want athletes and the people around them to understand about investment planning?

That it’s not complicated in principle, but it requires discipline in practice. The core of a sound investment strategy is straightforward: build liquidity, diversify broadly, invest consistently, and don’t let emotion or pressure override the plan. What makes it hard is that the sports world generates constant forces pulling in the other direction — large payments that feel like permission to spend, opportunities that feel like they can’t be missed, relationships that feel like they require financial participation.

Our role at TSG is to be the steady hand that keeps the strategy on track regardless of what’s happening around it. We view every athlete relationship as a long-term partnership — one that starts on signing day and extends well past the final chapter of their career. That’s what it means to invest like it has to last. Because it does.

Learn more about TSG’s approach to Sports & Entertainment wealth planning, or to explore the full range of investment and retirement planning services available through TSG Wealth Management at tsgwm.com/services.